Water → HCID 86585663, compound

HRID 1358919Notes

Reaction equation

HRID 1358919 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Cl:32])=[C:5]([C:7](=[N:30][OH:31])[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[CH:12]2[S:13][CH2:14][C:15]([S:23][C:24]2[S:25][C:26]([NH2:29])=[N:27][N:28]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.[Na].[C:34]([O:40][CH2:41]I)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36].O>CN(C=O)C>[CH3:36][C:35]([CH3:38])([CH3:37])[C:34]([O:40][CH2:41][O:21][C:20]([C:16]1[N:17]2[CH:12]([S:13][CH2:14][C:15]=1[S:23][C:24]1[S:25][C:26]([NH2:29])=[N:27][N:28]=1)[C@H:11]([NH:10][C:8](=[O:9])[C:7]([C:5]1[N:6]=[C:2]([NH2:1])[S:3][C:4]=1[Cl:32])=[N:30][OH:31])[C:18]2=[O:19])=[O:22])=[O:39]

Participants

6

Reactant 4

HCID 962WaterHCID 104401Iodomethyl pivalateHCID 5360545SodiumHCID 86585656HCID 86585656, compound

Product 1

HCID 86585663HCID 86585663, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of (7R)-7-[2-(2-amino-5-chlorothiazol-4-yl)-2-hydroxyiminoacetylamino]-3-(5-amino-[1,3,4]thiadiazol-2-ylsulfanyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, sodium salt (65 mg, 0.117 mmol) in DMF (0.3 mL) under nitrogen was added iodomethyl pivalate (31 mg, 0.128 mmol). After 1 h, water was added dropwise, and the precipitated product was removed by filtration to give 60.9 mg of the title compound.

Workup

  1. customthe precipitated product was removed by filtration

Sources & evidence

ORD record
ord-64072a8955d14d45924955e1465b4c13
Source dataset
uspto-grants-2003_07
Patent number
US06599893B2

Reaction notes

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