Acetate → (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-[1-(carbamoylcarbamoyl)cyclopentyl]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	1-Bromo-1-ureidocarbonylcyclopentane	HCID 12769266	—
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	—
Solvent	Ethanol	HCID 702	—
Product	(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-[1-(carbamoylcarbamoyl)cyclopentyl]oxyimino-2-(furan-2-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	HCID 12769247	85%

Reaction Steps

This was prepared from 1-bromo-1-ureidocarbonylcyclopentane and (6R,7R)-3-acetoxymethyl-7-[Z-2-(fur-2-yl)-2-hydroxyiminoacetamido]-ceph-3-em-4-carboxylic acid sodium salt, in a similar manner to Example 2. [α]D22 +95° (c 0.55, DMSO), λmax (EtOH) 275 nm (ε16,500), νmax (Nujol) 3420, 3300 (NH, NH2), 3700-2100 (bonded OH), 1788 (β-lactam), 1735 (acetate), 1710, 1690, 1565, 1550 cm-1 (CONH, CONHCONH2), τ (DMSO d6) 7.92 (OAc), 4.95, 5.28 (dd J 13) (3 --CH2), 6.23, 6.49 (dd, J 18) (2 --CH2), 4.71 (d, J=5) (6 H), 4.09 (dd J=5, 8) (7 H), 0.02 (d, J=8) (CONH), 2.11, 3.19, 3.32 (furyl), 7.9-8.3 (cyclopentyl), 0.65 (CONHCO), 2.17, 2.64 (CONH2). Yield: 85%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04208517
Source dataset	uspto-grants-1980_06
ORD ID	ord-84b2c82d75a844629ec99bab4614253f
Source note	uspto-grants-1980_06