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

HRID 1706830Notes

Reaction equation

HRID 1706830 reaction equation
Br[C:2]1([C:7]([NH:9][C:10]([NH2:12])=[O:11])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.[Na+].[C:14]([O:17][CH2:18][C:19]1[CH2:20][S:21][C@@H:22]2[C@H:29]([NH:30][C:31](=[O:40])/[C:32](/[C:35]3[O:36][CH:37]=[CH:38][CH:39]=3)=[N:33]\[OH:34])[C:28](=[O:41])[N:23]2[C:24]=1[C:25]([O-:27])=[O:26])(=[O:16])[CH3:15].C([O-])(=O)C>CS(C)=O.CCO>[C:14]([O:17][CH2:18][C:19]1[CH2:20][S:21][C@@H:22]2[C@H:29]([NH:30][C:31](=[O:40])/[C:32](/[C:35]3[O:36][CH:37]=[CH:38][CH:39]=3)=[N:33]\[O:34][C:2]3([C:7]([NH:9][C:10]([NH2:12])=[O:11])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]3)[C:28](=[O:41])[N:23]2[C:24]=1[C:25]([OH:27])=[O:26])(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 175AcetateHCID 127692661-Bromo-1-ureidocarbonylcyclopentaneHCID 23694123sodium (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

Product 1

HCID 12769247(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 acidYield 85%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 702EthanolSolvent

Procedure

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%.

Sources & evidence

ORD record
ord-84b2c82d75a844629ec99bab4614253f
Source dataset
uspto-grants-1980_06
Patent number
US04208517

Reaction notes

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