O-Phenylhydroxylamine hydrochloride → methyl (2Z)-2-(furan-2-yl)-2-[1-(phenoxycarbamoyl)cyclopentyl]oxyiminoacetate

HRID 851566Notes

Reaction equation

HRID 851566 reaction equation
[C:1]([C:4]1([O:9]/[N:10]=[C:11](/[C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)\[C:12]([O:14][CH3:15])=[O:13])[CH2:8][CH2:7][CH2:6][CH2:5]1)([OH:3])=O.Cl.[O:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[O:17]1[CH:18]=[CH:19][CH:20]=[C:16]1/[C:11](=[N:10]/[O:9][C:4]1([C:1](=[O:3])[NH:29][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH2:6][CH2:5]1)/[C:12]([O:14][CH3:15])=[O:13]

Participants

3

Reactant 2

HCID 6365179O-Phenylhydroxylamine hydrochlorideHCID 887367601-[(Z)-[1-(furan-2-yl)-2-methoxy-2-oxoethylidene]amino]oxycyclopentane-1-carboxylic acid

Product 1

HCID 20501531methyl (2Z)-2-(furan-2-yl)-2-[1-(phenoxycarbamoyl)cyclopentyl]oxyiminoacetateYield 44%

Procedure

This compound prepared from methyl Z-2-(carboxycyclopent-1-yloxyimino)-2-(fur-2-yl)acetate and phenoxyamine hydrochloride as described in Preparation 7(c), was purified by chromatography on silica gel plates in ethyl acetate-light petroleum b.p. 40°-60° (3:1 v/v). τ(DMSO d6) 2.5-3.1 (phenyl), 7.7-8.1, 8.1-8.5 (cyclopentyl), 2.0, 3.28, 3.02 (furyl), 6.03 (methyl). Yield 44%

Workup

  1. customwas purified by chromatography on silica gel plates in ethyl acetate-light petroleum b.p. 40°-60° (3:1 v/v)

Sources & evidence

ORD record
ord-d1eb09f14e4644afaa2c21b49ac57763
Source dataset
uspto-grants-1983_05
Patent number
US04385177

Reaction notes

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