HCID 86740397, compound → HCID 86740401, compound

HRID 978850Notes

Reaction equation

HRID 978850 reaction equation
ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:34][O:35][CH3:36])[C:12]([NH:14][C@H:15]2[C@@H:18]([O:19][C:20](=[O:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:17]([S:29]([O-:32])(=[O:31])=[O:30])[C:16]2=[O:33])=[O:13])[N:10]=1)=O.[Na+:37].CSC(=S)N.[Na]>O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:34][O:35][CH3:36])[C:12]([NH:14][C@H:15]2[C@@H:18]([O:19][C:20](=[O:28])[CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:17]([S:29]([O-:32])(=[O:30])=[O:31])[C:16]2=[O:33])=[O:13])[N:10]=1.[Na+:37]

Participants

4

Reactant 2

HCID 86740397HCID 86740397, compoundHCID 86740402HCID 86740402, compound

Product 1

HCID 86740401HCID 86740401, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.10 g of sodium (3S,4R)-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-4-phenylacetoxy-2-oxoazetidine-1-sulfonate in 7 ml of water is added under ice-cooling 0.027 g of sodium monomethyldithiocarbamate, and the mixture is stirred at room temperature for 1.5 hours. Insolubles are filtered off, and the filtrate is purified on an XAD-II column to yield 0.044 g of sodium (3S,4R)-3-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-4-phenylacetoxy-2-oxoazetidine-1-sulfonate.

Workup

  1. filtrationInsolubles are filtered off
  2. customthe filtrate is purified on an XAD-II column

Sources & evidence

ORD record
ord-5dc6776b8e994704b2f410df949df4cf
Source dataset
uspto-grants-1987_05
Patent number
US04665067

Reaction notes

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