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

HRID 648265Notes

Reaction equation

HRID 648265 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-8caf7176ebb04dfc8290e8a3d2c95b06
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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