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molecular formula C14H22N2O3 B1678819 (R)-(+)-Atenolol CAS No. 56715-13-0

(R)-(+)-Atenolol

Cat. No. B1678819
M. Wt: 266.34 g/mol
InChI Key: METKIMKYRPQLGS-GFCCVEGCSA-N
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Patent
US06982349B1

Procedure details

In order to prevent the reaction of produced atenolol with the optically active glycidyl ether (4) it is preferable to add the optically active glycidyl ether (4) to isopropyl amine in a solvent. The removal of excess isopropyl amine by distillation gave desired (S)-atenolol (1). Preferably, the distillation is carried out at atmospheric pressure at the initial stages and under reduced pressure at later stages, keeping the reaction mass temperature below 60° to 70° C., through out the distillation process. The crude residue may be purified, if required, by dissolving it in 1N HCl, treating this solution with activated charcoal, filtering the charcoal followed by treatment of alkali to precipitate the product. Thus, the solid product was isolated by conventional method such as filtration to get (S)-atenolol (1) of optical purity of 98% ee and above. If, necessary, the optically active (S)-atenolol (1) may be crystallized from an appropriate solvent such as water, alcohols, such as methanol, ethanol, isopropyl alcohol, butanol etc., ethers, such as diethyl ether, methyl tbutyl ether, diisopropyl ether or ketones, such as acetone, ethyl methyl ketone, methyl isobutyl ketone etc.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
[CH3:1][CH:2]([NH:4][CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[CH:13][CH:14]=1)[CH3:3].C(OCC1OC1)C1OC1.C(N)(C)C>>[CH3:3][CH:2]([NH:4][CH2:5][C@H:6]([OH:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[CH:11][CH:10]=1)[CH3:1]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)NCC(COC=1C=CC(=CC1)CC(=O)N)O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C1CO1)OCC1CO1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C1CO1)OCC1CO1
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C)(C)N

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
The removal of excess isopropyl amine
DISTILLATION
Type
DISTILLATION
Details
by distillation

Outcomes

Product
Name
Type
product
Smiles
CC(C)NC[C@@H](COC1=CC=C(C=C1)CC(=O)N)O

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
US06982349B1

Procedure details

In order to prevent the reaction of produced atenolol with the optically active glycidyl ether (4) it is preferable to add the optically active glycidyl ether (4) to isopropyl amine in a solvent. The removal of excess isopropyl amine by distillation gave desired (S)-atenolol (1). Preferably, the distillation is carried out at atmospheric pressure at the initial stages and under reduced pressure at later stages, keeping the reaction mass temperature below 60° to 70° C., through out the distillation process. The crude residue may be purified, if required, by dissolving it in 1N HCl, treating this solution with activated charcoal, filtering the charcoal followed by treatment of alkali to precipitate the product. Thus, the solid product was isolated by conventional method such as filtration to get (S)-atenolol (1) of optical purity of 98% ee and above. If, necessary, the optically active (S)-atenolol (1) may be crystallized from an appropriate solvent such as water, alcohols, such as methanol, ethanol, isopropyl alcohol, butanol etc., ethers, such as diethyl ether, methyl tbutyl ether, diisopropyl ether or ketones, such as acetone, ethyl methyl ketone, methyl isobutyl ketone etc.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
[CH3:1][CH:2]([NH:4][CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[CH:13][CH:14]=1)[CH3:3].C(OCC1OC1)C1OC1.C(N)(C)C>>[CH3:3][CH:2]([NH:4][CH2:5][C@H:6]([OH:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[CH:11][CH:10]=1)[CH3:1]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)NCC(COC=1C=CC(=CC1)CC(=O)N)O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C1CO1)OCC1CO1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C1CO1)OCC1CO1
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C)(C)N

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
The removal of excess isopropyl amine
DISTILLATION
Type
DISTILLATION
Details
by distillation

Outcomes

Product
Name
Type
product
Smiles
CC(C)NC[C@@H](COC1=CC=C(C=C1)CC(=O)N)O

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
US06982349B1

Procedure details

In order to prevent the reaction of produced atenolol with the optically active glycidyl ether (4) it is preferable to add the optically active glycidyl ether (4) to isopropyl amine in a solvent. The removal of excess isopropyl amine by distillation gave desired (S)-atenolol (1). Preferably, the distillation is carried out at atmospheric pressure at the initial stages and under reduced pressure at later stages, keeping the reaction mass temperature below 60° to 70° C., through out the distillation process. The crude residue may be purified, if required, by dissolving it in 1N HCl, treating this solution with activated charcoal, filtering the charcoal followed by treatment of alkali to precipitate the product. Thus, the solid product was isolated by conventional method such as filtration to get (S)-atenolol (1) of optical purity of 98% ee and above. If, necessary, the optically active (S)-atenolol (1) may be crystallized from an appropriate solvent such as water, alcohols, such as methanol, ethanol, isopropyl alcohol, butanol etc., ethers, such as diethyl ether, methyl tbutyl ether, diisopropyl ether or ketones, such as acetone, ethyl methyl ketone, methyl isobutyl ketone etc.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
[CH3:1][CH:2]([NH:4][CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[CH:13][CH:14]=1)[CH3:3].C(OCC1OC1)C1OC1.C(N)(C)C>>[CH3:3][CH:2]([NH:4][CH2:5][C@H:6]([OH:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[CH:11][CH:10]=1)[CH3:1]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)NCC(COC=1C=CC(=CC1)CC(=O)N)O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C1CO1)OCC1CO1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C1CO1)OCC1CO1
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C)(C)N

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
The removal of excess isopropyl amine
DISTILLATION
Type
DISTILLATION
Details
by distillation

Outcomes

Product
Name
Type
product
Smiles
CC(C)NC[C@@H](COC1=CC=C(C=C1)CC(=O)N)O

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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