O-Methylhydroxylamine → Methyl 2-(methoxycarbamoylcyclopent-1-yloxyimino)2-(fur-2-yl)acetate

HRID 851558Notes

Reaction equation

HRID 851558 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.[CH3:21][O:22][NH2:23].C(Br)(Br)Br>CS(C)=O>[CH3:21][O:22][NH:23][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)=[O:3]

Participants

5

Reactant 3

HCID 4113O-MethylhydroxylamineHCID 5558BromoformHCID 887367601-[(Z)-[1-(furan-2-yl)-2-methoxy-2-oxoethylidene]amino]oxycyclopentane-1-carboxylic acid

Product 1

HCID 54496876Methyl 2-(methoxycarbamoylcyclopent-1-yloxyimino)2-(fur-2-yl)acetateYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This compound was prepared from methyl Z-2-(carboxycyclopent-1-yloxyimino)-2-(fur-2-yl)acetate and methoxyamine as described in Preparation 7(c) νmax (CHBr3) 3400, 3350 (--NH--), 1740 (--CO2R), 1686 cm-1 (--CONH--), τ(DMSO d6), 6.4 (--OMe), --0.88 (--CONHO), 7.7-8.7 (cylopentyl), 2.1, 3.1, 3.3 (furyl), 6.1 (--CO2Me). Yield 75%

Sources & evidence

ORD record
ord-eb155584ad3c40b09446c649310d78fb
Source dataset
uspto-grants-1983_05
Patent number
US04385177

Reaction notes

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