Ethanol → (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-[4-[methyl(methylcarbamoyl)amino]-4-oxobutan-2-yl]oxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Participants

Role	Name	HCID	Charge
Reactant	Ethanol	HCID 702	—
Reactant	1-(2-Bromo-2-methylpropionyl)-1,3-dimethylurea	HCID 20334452	—
Reactant	sodium (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	HCID 23694123	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-[4-[methyl(methylcarbamoyl)amino]-4-oxobutan-2-yl]oxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	HCID 22811331	73%

Reaction Steps

This compound was prepared from 1-(2-bromo-2-methylpropionyl)-1,3-dimethylurea and (6R,7R)-3-acetoxymethyl-7-[Z-2-(fur-2-yl)-2-hydroxyiminoacetamido]-ceph-3-em-4-carboxylic acid sodium salt by the method described in Example 1. Yield 73%, λmax (EtOH) 274 nm (ε12,500), νmax (Nujol) 3300 (NH), 3700-2100 (bonded OH), 1789 (β-lactam), 1730 (CO2H), 1685, 1535 (CONH), τ(DMSO d6) 0.18 (CONH), 2.11, 3.28, 3.31 (furyl), 4.11, (7H), 4.77 (6H), 4.97, 6.29 (3--CH2), 6.29, 6.49 (2--CH2), 6.75 (NMe), 7.28 (NHMe), 7.93 (OAc), 8.41 (CMe2).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04208517
Source dataset	uspto-grants-1980_06
ORD ID	ord-e160bc9974e04e67889cda7b01838b89
Source note	uspto-grants-1980_06