2-(3-Chloro-4-hydroxyphenyl)-2-oxoacetic acid → (1-t-Butoxycarbonylethoxyimino)-2-(3-chloro-4-hydroxyphenyl)acetic acid

HRID 261667Notes

Reaction equation

HRID 261667 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[C:14]([O:18][C:19]([CH:21]([O:23][NH2:24])[CH3:22])=[O:20])([CH3:17])([CH3:16])[CH3:15]>>[C:14]([O:18][C:19]([CH:21]([O:23][N:24]=[C:9]([C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=1)[C:10]([OH:12])=[O:11])[CH3:22])=[O:20])([CH3:16])([CH3:15])[CH3:17]

Participants

3

Reactant 2

HCID 129611392-(3-Chloro-4-hydroxyphenyl)-2-oxoacetic acidHCID 19978722Tert-butyl 2-(aminooxy)propanoate

Product 1

HCID 136081925(1-t-Butoxycarbonylethoxyimino)-2-(3-chloro-4-hydroxyphenyl)acetic acidYield 96.3%

Procedure

2-(3-Chloro-4-hydroxyphenyl)glyoxylic acid (2.0 g.) and O-(1-t-butoxycarbonylethyl)hydroxylamine (3.2 g.) were reacted according to a similar manner to that of Preparation (5-7) to give 2-(1-t-butoxycarbonylethoxyimino)-2-(3-chloro-4-hydroxyphenyl)acetic acid (syn isomer) (3.3 g.), mp 148° to 151° C.

Sources & evidence

ORD record
ord-5d91cc505b96455b83904ccae56a6fc9
Source dataset
uspto-grants-1979_08
Patent number
US04166115

Reaction notes

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