Ethanol → tert-butyl 1-[(Z)-[1-(furan-2-yl)-2-methoxy-2-oxoethylidene]amino]oxycyclobutane-1-carboxylate

HRID 851560Notes

Reaction equation

HRID 851560 reaction equation
[C:1]([O:5][C:6]([C:8]1([O:12]/[N:13]=[C:14](/[C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)\[C:15]([OH:17])=[O:16])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23]CO.C1CCC1>CS(C)=O>[C:1]([O:5][C:6]([C:8]1([O:12]/[N:13]=[C:14](/[C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)\[C:15]([O:17][CH3:23])=[O:16])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 9250CyclobutaneHCID 20501549(2Z)-2-(furan-2-yl)-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]cyclobutyl]oxyiminoacetic acid

Product 1

HCID 20501539tert-butyl 1-[(Z)-[1-(furan-2-yl)-2-methoxy-2-oxoethylidene]amino]oxycyclobutane-1-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This compound was prepared from Z-2-(1-tertbutyloxycarbonylcyclobutyloxyimino)-2-(fur-2-yl)acetic acid as described in Preparation 7(a). λmax (EtOH) 281.5 nm (ε17,000), νmax (Nujol) 1745 (--CO2R), 1723 cm-1 (α,β-unsaturated --CO2R), τ(DMSO d6) 8.59 (--C(Me)3), 7.3-8.4 (cyclobutane), 2.1, 3.15, 3.35 (furyl), 6.09 (--CO2CH3). Yield 98%.

Sources & evidence

ORD record
ord-aa2932c0775a463c85fbb81726d2ea24
Source dataset
uspto-grants-1983_05
Patent number
US04385177

Reaction notes

Loading…