Acetic Acid → N-formyl,N-(4-chlorophenyl)valine

HRID 1389360Notes

Reaction equation

HRID 1389360 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[CH:16]([O:18][C:19](=O)[CH3:20])=[O:17].C(O)(=O)C.[CH:26]([OH:28])=O>>[CH:16]([N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:17].[C:19]([C:26]([N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:28])(=[O:18])[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 284Formic AcidHCID 75269Acetic-formic anhydrideHCID 13796078N-(p-chlorophenyl)valine

Product 2

HCID 57019758N-formyl,N-(4-chlorophenyl)valineHCID 57070001N-acetylformyl,N-(4-chlorophenyl)valine

Procedure

A mixture of the m-phenoxybenzyl ester of N-(4-chlorophenyl)valine (1.22 mmole), acetic formic anhydride in acetic acid (23.8 mmole, 2.1 g) and formic acid (1.5 ml) is stirred overnight at RT under nitrogen. The reaction product is concentrated and then subjected to prep. TLC eluting with 20% ethylacetate/hexane to yield the m-phenoxybenzyl ester of N-formyl,N-(4-chlorophenyl)valine, MS m/e 437 (M+, 8.1), 182 (100).

Workup

  1. concentrationThe reaction product is concentrated
  2. washTLC eluting with 20% ethylacetate/hexane

Sources & evidence

ORD record
ord-bdfe1b327dba4b8d96f0900e06ee5db7
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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