Water → HCID 131713549, compound

HRID 1262774Notes

Reaction equation

HRID 1262774 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:24][O:25][CH2:26][C:27]([O:29][CH:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[C:8]([NH:10][CH:11]2[C:22](=[O:23])[N:13]3[C:14]([C:19]([O-:21])=[S:20])=[C:15]([CH3:18])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:44]([O:50][CH2:51]I)(=[O:49])[C:45]([CH3:48])([CH3:47])[CH3:46].C(OCC)(=O)C.O>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:24][O:25][CH2:26][C:27]([O:29][CH:30]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:28])[C:8]([NH:10][CH:11]2[C:22](=[O:23])[N:13]3[C:14]([C:19]([O:21][CH2:51][O:50][C:44](=[O:49])[C:45]([CH3:48])([CH3:47])[CH3:46])=[S:20])=[C:15]([CH3:18])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 104401Iodomethyl pivalateHCID 131713555HCID 131713555, compound

Product 1

HCID 131713549HCID 131713549, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of sodium 7-[2-(2-aminothiazol-4-yl)-2-benzhydryloxycarbonylmethoxyiminoacetamido]-3-methylthio-3-cephem-4-carboxylate (syn isomer) (4.0 g) in dimethylformamide (40 ml) was added a solution of pivaloyloxymethyl iodide (1.5 g) in dimethylformamide (4.5 ml) at 0° C. and the mixture was stirred for 15 minutes at the same temperature. Ethyl acetate (150 ml) and water (100 ml) were added to the reaction mixture. The separated organic layer was washed with saturated aqueous sodium bicarbonate and water, dried over magnesium sulfate and evaporated to give pivaloyloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-benzhydryloxycarbonylmethoxyiminoacetamido]-3-methylthio-3-cephem-4-carboxylate (syn isomer) (3.22 g).

Workup

  1. washThe separated organic layer was washed with saturated aqueous sodium bicarbonate and water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-bb6935baf1bc4a659e3896374ff2d43f
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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