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

HRID 1706834Notes

Reaction equation

HRID 1706834 reaction equation
Br[C:2]([CH3:12])([CH3:11])[C:3]([NH:5][C:6]([N:8]([CH3:10])[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].CCO.C([O-])(=O)C>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][C:2]([C:3]([NH:5][C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[O:4])([CH3:12])[CH3:11])/[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

6

Reactant 4

HCID 175AcetateHCID 702EthanolHCID 127692671-(2-Bromo-2-methylpropionyl)-3,3-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 12769255(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 acidYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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%.

Sources & evidence

ORD record
ord-a38b484dc0f947ccbc46c5ffbbbecb02
Source dataset
uspto-grants-1980_06
Patent number
US04208517

Reaction notes

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