Synthesis routes of 2-[4-(Benzyloxy)-2-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetamide

2-[4-(Benzyloxy)-2-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetamide

Cat. No. B8628011

: 113896-94-9

M. Wt: 246.26 g/mol

InChI Key: CPMIVIBDTJGVDA-UHFFFAOYSA-N

Attention: For research use only. Not for human or veterinary use.

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Patent

US04849528

Procedure details

3.00 g of 4-benzyloxy-3-pyrrolin-2-on-1-yl acetamide was dissolved in 30 ml of concentrated acetic acid and mixed with 240 mg of palladium 5 percent on activated carbon and 24 mg of platinum oxide. Hydrogenolysis and hydrogenation at 15 bars of hydrogen pressure and room temperature were performed for 65 hours. Then filtering off from the catalyst and evaporation of the solvent were performed. The residue was picked up in H2O and allowed to run over 5.0 g of weakly basic ion exchanger. The water was distilled off and the residue mixed with 10 ml of acetone. 1.53 g of nearly white 4-hydroxypyrrolidin-2-on-1-yl acetamide with a melting point of 163.5° to 165.7° C. was obtained.

Name

4-benzyloxy-3-pyrrolin-2-on-1-yl acetamide

Quantity

3 g

Type

reactant

Reaction Step One

Name

acetic acid

Quantity

30 mL

Type

solvent

Reaction Step One

[H][H]

Name

hydrogen

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

palladium

Quantity

240 mg

Type

catalyst

Reaction Step Three

Name

platinum oxide

Quantity

24 mg

Type

catalyst

Reaction Step Three

Name

4-hydroxypyrrolidin-2-on-1-yl acetamide

Identifiers

REACTION_CXSMILES

C([O:8][C:9]1[CH2:13][N:12]([CH2:14][C:15]([NH2:17])=[O:16])[C:11](=[O:18])[CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd].[Pt]=O>[OH:8][CH:9]1[CH2:13][N:12]([CH2:14][C:15]([NH2:17])=[O:16])[C:11](=[O:18])[CH2:10]1

Inputs

Step One

Name	4-benzyloxy-3-pyrrolin-2-on-1-yl acetamide
Quantity	3 g
Type	reactant
Smiles	C(C1=CC=CC=C1)OC1=CC(N(C1)CC(=O)N)=O

Name	acetic acid
Quantity	30 mL
Type	solvent
Smiles	C(C)(=O)O

Step Two

[H][H]

Name	hydrogen
Quantity	0 (± 1) mol
Type	reactant
Smiles	[H][H]

Step Three

Name	palladium
Quantity	240 mg
Type	catalyst
Smiles	[Pd]

Name	platinum oxide
Quantity	24 mg
Type	catalyst
Smiles	[Pt]=O

Conditions

Other

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

Workups

FILTRATION

Type	FILTRATION
Details	Then filtering off from the catalyst and evaporation of the solvent

DISTILLATION

Type	DISTILLATION
Details	The water was distilled off

ADDITION

Type	ADDITION
Details	the residue mixed with 10 ml of acetone

Outcomes

Product

Name	4-hydroxypyrrolidin-2-on-1-yl acetamide
Type	product
Smiles	OC1CC(N(C1)CC(=O)N)=O

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.