Water → 2-(Phenylcarbamoyl)acetic acid

HRID 1373080Notes

Reaction equation

HRID 1373080 reaction equation
C[O:2][C:3](=[O:14])[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[OH-].[Li+].O1CCCC1.O>CO>[C:8]1([NH:7][C:5](=[O:6])[CH2:4][C:3]([OH:14])=[O:2])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 564817HCID 564817, compound

Product 1

HCID 2565932-(Phenylcarbamoyl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrolysis of the N-Phenyl-malonamic acid methyl ester from step a (6.8 g, 35.2 mmol) with lithium hydroxide (8.9 g, 212 mmol) in a mixture of methanol (160 mL), tetrahydrofuran (160 mL) and water (160 mL) at room temperature for 3 h, afforded the title acid (5.76 g, 91.3%). 1H NMR (400 MHz, DMSO-d6) δ: 12.64 (s, 1H), 10.11 (s, 1H), 7.58 (d, 2H), 7.31 (t, 2H), 7.06 (t, 1H), 3.36 (s, 2H).

Workup

  1. customafforded the title acid (5.76 g, 91.3%)

Sources & evidence

ORD record
ord-bec996d1d0c94a9bb8a18ddc1fc40451
Source dataset
uspto-grants-2007_01
Patent number
US07160902B2

Reaction notes

Loading…