Acetate → (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-[2-(carbamoylamino)-2-oxoethoxy]imino-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	n-Carbamoyl-2-iodoacetamide	HCID 234533	—
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-[2-(carbamoylamino)-2-oxoethoxy]imino-2-(furan-2-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	HCID 12769257	34%

Reaction Steps

This compound was prepared from iodoacetylurea 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) 274 nm (ε 17,300), νmax (Nujol) 3420, 3260 (--NH--, --NH2), 3700-2100 (bonded OH), 1780 (β-lactam), 1720(--CO2H, acetate), 1700, 1570, 1545 cm-1 (CONH, CONH2), τ (DMSO d6) 2.11, 3.3, 3.18 (furyl), 5.28 (--O--CH2 --), 0.09 (--CONHCO--), 2.5 (CONH2), 0.11 (CONH), 4.1 (7 H), 4.78 (6 H), 6.29, 6.51 (2--CH2), 4.95, 5.28 (3 --CH2), 7.93 (CH3CO--). Yield: 34%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04208517
Source dataset	uspto-grants-1980_06
ORD ID	ord-91be911768f14cd886067195a7eff552
Source note	uspto-grants-1980_06