Sodium Hydroxide → HCID 13242795, compound

HRID 1655716Notes

Reaction equation

HRID 1655716 reaction equation
[CH2:1]([CH:8]([C:12](=[O:19])C1CNCCO1)[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC(=O)C(CC1C=CC=CC=1)C(O)=O.[CH2:35]([O:42][NH2:43])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[OH-].[Na+]>O.CO>[CH2:35]([O:42][NH:43][C:12]([CH:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]([OH:11])=[O:10])=[O:19])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 102313O-BenzylhydroxylamineHCID 10921701HCID 10921701, compoundHCID 19790783HCID 19790783, compound

Product 1

HCID 13242795HCID 13242795, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a manner analogous to that described for α-benzyltetrahydro-β-oxo-4H-1,4-oxazinepropionic acid, benzylmalonic acid monomethyl ester was amidated with O-benzylhydroxylamine and the resulting product [MS: 314 (M+H)+ ] was saponified with 1N sodium hydroxide solution in a 9:1 mixture of methanol and water to the corresponding acid. Recrystallization of the crude product from methanol/methylene chloride/ether yielded α-[(benzyloxy)carbamoyl]hydrocinnamic acid of melting point 147°.

Workup

  1. customRecrystallization of the crude product from methanol/methylene chloride/ether

Sources & evidence

ORD record
ord-eeeedf7302924a81adf636345cd0960c
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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