Acetate → (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-[1-(dimethylcarbamoylamino)-2-methyl-1-oxopropan-2-yl]oxyimino-2-(furan-2-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Participants

Role	Name	HCID	Charge
Reactant	Acetate	HCID 175	—
Reactant	Ethanol	HCID 702	—
Reactant	1-(2-Bromo-2-methylpropionyl)-3,3-dimethylurea	HCID 12769267	—
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-[1-(dimethylcarbamoylamino)-2-methyl-1-oxopropan-2-yl]oxyimino-2-(furan-2-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	HCID 12769255	59%

Reaction Steps

This compound was prepared from 1-(2-bromo-2-methylpropionyl)-3,3-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. λmax (EtOH) 275 nm (ε 16,500), νmax (Nujol) 3260 (NH), 3700-2100 (bonded OH), 1788 (β-lactam), 1735 (acetate), 1720 (--CO2H), 1670, 1540 cm-1 (--CONH), τ (DMSO d6) 7.09 (N(Me)2), 0.97 (--CONHCO--), 8.5 (C(Me)2), 2.06, 3.28, 3.16 (furyl), 0.18 (CONH), 4.01 (7 H), 4.71 (6 H), 6.25, 6.46 (2--CH2 --), 4.97, 5.29 (3--CH2 --), 7.98 (CH3CO). Yield: 59%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04208517
Source dataset	uspto-grants-1980_06
ORD ID	ord-a38b484dc0f947ccbc46c5ffbbbecb02
Source note	uspto-grants-1980_06