Synthesis routes of Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate

Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate

Cat. No. B144351

: 62613-81-4

M. Wt: 187.19 g/mol

InChI Key: YDBONCLBTWFUPF-UHFFFAOYSA-N

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

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Patent

US04629797

Procedure details

A solution of 7.1 g ethyl 4-hydroxy-2-oxo-1-pyrrolidineacetate obtained in Example 12, in 7.1 ml ammonia solution (d25 =0.90) is stirred at ambient temperature for 15 h. It is then diluted with 140 ml acetone and the mixture is stirred at ambient temperature until the gum that precipitates solidifies into white crystals. On filtering in vacuo and drying, 4-hydroxy-2-oxo-1-pyrrolidineacetamide is obtained, m.p. 160°-162° C.

Name

ethyl 4-hydroxy-2-oxo-1-pyrrolidineacetate

Quantity

7.1 g

Type

reactant

Reaction Step One

Name

ammonia

Quantity

7.1 mL

Type

reactant

Reaction Step One

Name

acetone

Quantity

140 mL

Type

solvent

Reaction Step Two

Name

4-hydroxy-2-oxo-1-pyrrolidineacetamide

Identifiers

REACTION_CXSMILES

[OH:1][CH:2]1[CH2:6][N:5]([CH2:7][C:8](OCC)=[O:9])[C:4](=[O:13])[CH2:3]1.[NH3:14]>CC(C)=O>[OH:1][CH:2]1[CH2:6][N:5]([CH2:7][C:8]([NH2:14])=[O:9])[C:4](=[O:13])[CH2:3]1

Inputs

Step One

Name	ethyl 4-hydroxy-2-oxo-1-pyrrolidineacetate
Quantity	7.1 g
Type	reactant
Smiles	OC1CC(N(C1)CC(=O)OCC)=O

Name	ammonia
Quantity	7.1 mL
Type	reactant
Smiles	N

Step Two

Name	acetone
Quantity	140 mL
Type	solvent
Smiles	CC(=O)C

Conditions

Temperature

Control Type

AMBIENT

Stirring

Type	CUSTOM
Details	the mixture is stirred at ambient temperature until the gum
Rate	UNSPECIFIED
RPM	0

Other

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

Workups

CUSTOM

Type	CUSTOM
Details	that precipitates

FILTRATION

Type	FILTRATION
Details	On filtering in vacuo

CUSTOM

Type	CUSTOM
Details	drying

Outcomes

Product

Name	4-hydroxy-2-oxo-1-pyrrolidineacetamide
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.