Synthesis routes of 4-[(4-methoxyphenyl)formamido]butanoic acid

4-[(4-methoxyphenyl)formamido]butanoic acid

货号 B1200448

Key on ui cas rn: 72432-14-5

分子量: 237.25 g/mol

InChI 键: DZTVZKSCFQIBMV-UHFFFAOYSA-N

注意: 仅供研究使用。不适用于人类或兽医用途。

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Patent

US04369139

Procedure details

10.2 g. of p-methoxybenzoyl chloride are added at 30° C. in one portion while stirring well to 30.9 g. of 4-amino-butyric acid, 24.0 g. of sodium hydroxide and 300 ml. of ion-free water. After 2 hours, the mixture is acidified with 75 ml. of concentrated hydrochloric acid at a temperature below 10° C. The precipitate is filtered off, washed ion-free with water, dried in a drying oven at 65° C. over phosphorus pentoxide and then recrystallized from 45 ml. of acetone/low-boiling petroleum ether (3:1). There is obtained 4-(p-methoxybenzoylamino)butyric acid having a melting point of 120.5°-122° C.

Name

p-methoxybenzoyl chloride

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

4-amino-butyric acid

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

sodium hydroxide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

hydrochloric acid

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

water

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Five

Name

4-(p-methoxybenzoylamino)butyric acid

Identifiers

REACTION_CXSMILES

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[NH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].[OH-].[Na+].Cl>O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:8])=[CH:5][CH:4]=1 |f:2.3|

Inputs

Step One

Name	p-methoxybenzoyl chloride
Quantity	0 (± 1) mol
Type	reactant
Smiles	COC1=CC=C(C(=O)Cl)C=C1

Step Two

Name	4-amino-butyric acid
Quantity	0 (± 1) mol
Type	reactant
Smiles	NCCCC(=O)O

Step Three

Name	sodium hydroxide
Quantity	0 (± 1) mol
Type	reactant
Smiles	[OH-].[Na+]

Step Four

Name	hydrochloric acid
Quantity	0 (± 1) mol
Type	reactant
Smiles	Cl

Step Five

Name	water
Quantity	0 (± 1) mol
Type	solvent
Smiles	O

Conditions

Stirring

Type	CUSTOM
Details	while stirring well to 30.9 g
Rate	UNSPECIFIED
RPM	0

Other

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

Workups

CUSTOM

Type	CUSTOM
Details	at a temperature below 10° C

FILTRATION

Type	FILTRATION
Details	The precipitate is filtered off

WASH

Type	WASH
Details	washed ion-free with water

DRY_WITH_MATERIAL

Type	DRY_WITH_MATERIAL
Details	dried in a drying oven at 65° C. over phosphorus pentoxide

CUSTOM

Type	CUSTOM
Details	recrystallized from 45 ml

Outcomes

Product

Details

Reaction Time

2 h

Name	4-(p-methoxybenzoylamino)butyric acid
Type	product
Smiles	COC1=CC=C(C(=O)NCCCC(=O)O)C=C1

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.