Dimethyl Sulfoxide → 1-[(Z)-[1-(furan-2-yl)-2-methoxy-2-oxoethylidene]amino]oxycyclobutane-1-carboxylic acid

HRID 851561Notes

Reaction equation

C(OC(O[C:9]1([O:13]/[N:14]=[C:15](/[C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)\[C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11][CH2:10]1)=O)(C)(C)C.C[CH2:26][OH:27].C1CCC1.CS(C)=[O:34]>>[C:26]([C:9]1([O:13]/[N:14]=[C:15](/[C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)\[C:16]([O:18][CH3:19])=[O:17])[CH2:10][CH2:11][CH2:12]1)([OH:27])=[O:34]

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 702Ethanol

HCID 9250Cyclobutane

HCID 20501519methyl (2Z)-2-(furan-2-yl)-2-[1-[(2-methylpropan-2-yl)oxycarbonyloxy]cyclobutyl]oxyiminoacetate

Product 1

HCID 127743501-[(Z)-[1-(furan-2-yl)-2-methoxy-2-oxoethylidene]amino]oxycyclobutane-1-carboxylic acidYield 94%

Procedure

This compound was prepared from methyl Z-2-(1-tert-butyloxycarbonyloxycyclobutyloxyimino)-2-(fur-2-yl)acetate as described in Preparation 7(b), m.p. 133°-134°. λmax (EtOH) 284 nm (ε15,900), νmax (Nujol) 3500-2100 (bonded OH), 1750 (CO2H), 1708 cm-1 (α,β-unsaturated --CO2R), τ(DMSO d6) 7.2-8.5 (cyclobutane), 2.1, 3.12, 3.33 (furyl), 6.09 (--CO2CH3). Yield 94%

Sources & evidence

ORD record: ord-fc50e413c5f44158aa00edf8c9c810f6
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04385177

Reaction notes

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