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

HRID 1706837Notes

Reaction equation

HRID 1706837 reaction equation
Br[C:2]([CH3:12])(C)[C:3]([N:5]([CH3:10])[C:6]([NH:8][CH3:9])=[O:7])=[O:4].[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].[CH3:42]CO>CS(C)=O>[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](=[N:33]\[O:34][CH:12]([CH2:2][C:3]([N:5]([CH3:10])[C:6]([NH:8][CH3:9])=[O:7])=[O:4])[CH3:42])/[C:35]3[O:36][CH:37]=[CH:38][CH:39]=3)[C:28](=[O:41])[N:23]2[C:24]=1[C:25]([OH:27])=[O:26])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 203344521-(2-Bromo-2-methylpropionyl)-1,3-dimethylureaHCID 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 22811331(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 acidYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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).

Sources & evidence

ORD record
ord-e160bc9974e04e67889cda7b01838b89
Source dataset
uspto-grants-1980_06
Patent number
US04208517

Reaction notes

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