Ethanol → (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-[2-methyl-1-(methylcarbamoylamino)-1-oxopropan-2-yl]oxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1706831Notes

Reaction equation

HRID 1706831 reaction equation
Br[C:2]([CH3:11])([CH3:10])[C:3]([NH:5][C:6]([NH:8][CH3:9])=[O:7])=[O:4].[Na+].[C:13]([O:16][CH2:17][C:18]1[CH2:19][S:20][C@@H:21]2[C@H:28]([NH:29][C:30](=[O:39])/[C:31](/[C:34]3[O:35][CH:36]=[CH:37][CH:38]=3)=[N:32]\[OH:33])[C:27](=[O:40])[N:22]2[C:23]=1[C:24]([O-:26])=[O:25])(=[O:15])[CH3:14].CCO>CS(C)=O>[C:13]([O:16][CH2:17][C:18]1[CH2:19][S:20][C@@H:21]2[C@H:28]([NH:29][C:30](=[O:39])/[C:31](/[C:34]3[O:35][CH:36]=[CH:37][CH:38]=3)=[N:32]\[O:33][C:2]([C:3]([NH:5][C:6]([NH:8][CH3:9])=[O:7])=[O:4])([CH3:11])[CH3:10])[C:27](=[O:40])[N:22]2[C:23]=1[C:24]([OH:26])=[O:25])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 203344561-(2-Bromo-2-methylpropionyl)-3-methylureaHCID 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 12769251(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-[2-methyl-1-(methylcarbamoylamino)-1-oxopropan-2-yl]oxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 76%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

This compound was prepared from 1-(2-bromo-2-methylpropionyl)-3-methylurea 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. [α]D22 +84.6° (c 0.65, DMSO), λmax (EtOH) 274 nm (ε 16,900), νmax (Nujol) 3340 (NH), 3700-2100 (bonded OH), 1790 (β-lactam), 1740 (OCOCH3), 1700 (CO2H), 1690, 1540 cm-1 (--CONH--, --CONHCONH--), τ (DMSO d6) 2.25, 3.2, 3.35 (fur-2-yl), 8.51, 8.52 (C(Me)2), 0.5 (--CONHCO), 1.75 (CONHMe), 7.28 (CONHMe), 4.1 (7 H), 4.75 (6 H), 6.28, 6.50 (2 CH2), 4.97, 5.29 (3 CH2), 7.9 (OCOCH3). Yield: 76%.

Sources & evidence

ORD record
ord-a2ab8c885f2b491687779ef65163019f
Source dataset
uspto-grants-1980_06
Patent number
US04208517

Reaction notes

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