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molecular formula C16H15F6N5O B1680988 Sitagliptin CAS No. 486460-32-6

Sitagliptin

Cat. No. B1680988
M. Wt: 407.31 g/mol
InChI Key: MFFMDFFZMYYVKS-SECBINFHSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08476437B2

Procedure details

Dibenzoyl-D-tartaric acid salt of 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine was prepared by reacting Dibezoyl-D-tartaric acid monohydrate and 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine in molar equivalent ratio in methanol. The salt was filtered off and filtrate was collected. Solvent was distilled out from the filtrate to obtain enantiomerically enriched desired isomer which was basified in aq. methanol by using NaHCO3. Solvent was again distilled out. The residue was dissolved in ethyl acetate and washed with water and brine solution. Ethyl acetate extract was collected and dried over anhydrous sodium sulfate. Ethyl acetate was distilled out to obtain (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (% Purity by HPLC-88%, % Chiral purity by HPLC-90.0%).
Name
Dibezoyl-D-tartaric acid monohydrate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Five

Identifiers

REACTION_CXSMILES
O.[C:2]([C@:10]([C:25]([OH:27])=[O:26])([OH:24])[C@:11]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([OH:15])[C:12]([OH:14])=[O:13])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][CH:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41].C([O-])(O)=O.[Na+]>CO>[C:16]([C@:11]([C:12]([OH:14])=[O:13])([OH:15])[C@:10]([C:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([OH:24])[C:25]([OH:27])=[O:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][CH:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41].[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][C@H:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41] |f:0.1,3.4|

Inputs

Step One
Name
Dibezoyl-D-tartaric acid monohydrate
Quantity
0 (± 1) mol
Type
reactant
Smiles
O.C(C1=CC=CC=C1)(=O)[C@@]([C@@](C(=O)O)(O)C(C1=CC=CC=C1)=O)(O)C(=O)O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(=O)(O)[O-].[Na+]
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Five
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

FILTRATION
Type
FILTRATION
Details
The salt was filtered off
CUSTOM
Type
CUSTOM
Details
filtrate was collected
DISTILLATION
Type
DISTILLATION
Details
Solvent was distilled out from the filtrate
CUSTOM
Type
CUSTOM
Details
to obtain enantiomerically
DISTILLATION
Type
DISTILLATION
Details
Solvent was again distilled out
DISSOLUTION
Type
DISSOLUTION
Details
The residue was dissolved in ethyl acetate
WASH
Type
WASH
Details
washed with water and brine solution
EXTRACTION
Type
EXTRACTION
Details
Ethyl acetate extract
CUSTOM
Type
CUSTOM
Details
was collected
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over anhydrous sodium sulfate
DISTILLATION
Type
DISTILLATION
Details
Ethyl acetate was distilled out

Outcomes

Product
Name
Type
product
Smiles
C(C1=CC=CC=C1)(=O)[C@@]([C@@](C(=O)O)(O)C(C1=CC=CC=C1)=O)(O)C(=O)O
Name
Type
product
Smiles
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
Name
Type
product
Smiles
O=C(C[C@@H](CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US08476437B2

Procedure details

Dibenzoyl-D-tartaric acid salt of 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine was prepared by reacting Dibezoyl-D-tartaric acid monohydrate and 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine in molar equivalent ratio in methanol. The salt was filtered off and filtrate was collected. Solvent was distilled out from the filtrate to obtain enantiomerically enriched desired isomer which was basified in aq. methanol by using NaHCO3. Solvent was again distilled out. The residue was dissolved in ethyl acetate and washed with water and brine solution. Ethyl acetate extract was collected and dried over anhydrous sodium sulfate. Ethyl acetate was distilled out to obtain (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (% Purity by HPLC-88%, % Chiral purity by HPLC-90.0%).
Name
Dibezoyl-D-tartaric acid monohydrate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Five

Identifiers

REACTION_CXSMILES
O.[C:2]([C@:10]([C:25]([OH:27])=[O:26])([OH:24])[C@:11]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([OH:15])[C:12]([OH:14])=[O:13])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][CH:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41].C([O-])(O)=O.[Na+]>CO>[C:16]([C@:11]([C:12]([OH:14])=[O:13])([OH:15])[C@:10]([C:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([OH:24])[C:25]([OH:27])=[O:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][CH:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41].[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][C@H:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41] |f:0.1,3.4|

Inputs

Step One
Name
Dibezoyl-D-tartaric acid monohydrate
Quantity
0 (± 1) mol
Type
reactant
Smiles
O.C(C1=CC=CC=C1)(=O)[C@@]([C@@](C(=O)O)(O)C(C1=CC=CC=C1)=O)(O)C(=O)O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(=O)(O)[O-].[Na+]
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Five
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

FILTRATION
Type
FILTRATION
Details
The salt was filtered off
CUSTOM
Type
CUSTOM
Details
filtrate was collected
DISTILLATION
Type
DISTILLATION
Details
Solvent was distilled out from the filtrate
CUSTOM
Type
CUSTOM
Details
to obtain enantiomerically
DISTILLATION
Type
DISTILLATION
Details
Solvent was again distilled out
DISSOLUTION
Type
DISSOLUTION
Details
The residue was dissolved in ethyl acetate
WASH
Type
WASH
Details
washed with water and brine solution
EXTRACTION
Type
EXTRACTION
Details
Ethyl acetate extract
CUSTOM
Type
CUSTOM
Details
was collected
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over anhydrous sodium sulfate
DISTILLATION
Type
DISTILLATION
Details
Ethyl acetate was distilled out

Outcomes

Product
Name
Type
product
Smiles
C(C1=CC=CC=C1)(=O)[C@@]([C@@](C(=O)O)(O)C(C1=CC=CC=C1)=O)(O)C(=O)O
Name
Type
product
Smiles
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
Name
Type
product
Smiles
O=C(C[C@@H](CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US08476437B2

Procedure details

Dibenzoyl-D-tartaric acid salt of 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine was prepared by reacting Dibezoyl-D-tartaric acid monohydrate and 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine in molar equivalent ratio in methanol. The salt was filtered off and filtrate was collected. Solvent was distilled out from the filtrate to obtain enantiomerically enriched desired isomer which was basified in aq. methanol by using NaHCO3. Solvent was again distilled out. The residue was dissolved in ethyl acetate and washed with water and brine solution. Ethyl acetate extract was collected and dried over anhydrous sodium sulfate. Ethyl acetate was distilled out to obtain (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (% Purity by HPLC-88%, % Chiral purity by HPLC-90.0%).
Name
Dibezoyl-D-tartaric acid monohydrate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Five

Identifiers

REACTION_CXSMILES
O.[C:2]([C@:10]([C:25]([OH:27])=[O:26])([OH:24])[C@:11]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([OH:15])[C:12]([OH:14])=[O:13])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][CH:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41].C([O-])(O)=O.[Na+]>CO>[C:16]([C@:11]([C:12]([OH:14])=[O:13])([OH:15])[C@:10]([C:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([OH:24])[C:25]([OH:27])=[O:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][CH:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41].[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][C@H:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41] |f:0.1,3.4|

Inputs

Step One
Name
Dibezoyl-D-tartaric acid monohydrate
Quantity
0 (± 1) mol
Type
reactant
Smiles
O.C(C1=CC=CC=C1)(=O)[C@@]([C@@](C(=O)O)(O)C(C1=CC=CC=C1)=O)(O)C(=O)O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(=O)(O)[O-].[Na+]
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Five
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

FILTRATION
Type
FILTRATION
Details
The salt was filtered off
CUSTOM
Type
CUSTOM
Details
filtrate was collected
DISTILLATION
Type
DISTILLATION
Details
Solvent was distilled out from the filtrate
CUSTOM
Type
CUSTOM
Details
to obtain enantiomerically
DISTILLATION
Type
DISTILLATION
Details
Solvent was again distilled out
DISSOLUTION
Type
DISSOLUTION
Details
The residue was dissolved in ethyl acetate
WASH
Type
WASH
Details
washed with water and brine solution
EXTRACTION
Type
EXTRACTION
Details
Ethyl acetate extract
CUSTOM
Type
CUSTOM
Details
was collected
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over anhydrous sodium sulfate
DISTILLATION
Type
DISTILLATION
Details
Ethyl acetate was distilled out

Outcomes

Product
Name
Type
product
Smiles
C(C1=CC=CC=C1)(=O)[C@@]([C@@](C(=O)O)(O)C(C1=CC=CC=C1)=O)(O)C(=O)O
Name
Type
product
Smiles
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
Name
Type
product
Smiles
O=C(C[C@@H](CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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