Monomethyl sulfate → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

HRID 2399846Notes

Reaction equation

HRID 2399846 reaction equation
COS(O)(=O)=O.COCOC.C(=O)(OC)OC.C[C:19]([O:21][CH2:22][C:23]1[CH2:32][S:31][C@@H:26]2[C@H:27]([NH2:30])[C:28](=[O:29])[N:25]2[C:24]=1[C:33]([OH:35])=[O:34])=O>CO>[NH2:30][CH:27]1[C:28](=[O:29])[N:25]2[C:24]([C:33]([OH:35])=[O:34])=[C:23]([CH2:22][O:21][CH3:19])[CH2:32][S:31][C@H:26]12

Participants

6

Reactant 4

HCID 6412Monomethyl sulfateHCID 8020DimethoxymethaneHCID 12021Dimethyl CarbonateHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 128330237-Amino-3-methoxymethyl-3-cephem-4-carboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

20.28 g of a methanolic solution of methoxysulfonic acid (prepared as described in Preparation 2), 1.77 g of methanol and 2.30 g of methylal (prepared as described in Preparation 5) were added to 30 ml of dimethyl carbonate. The mixture was cooled to 10° C., and 2.74 g of 7-ACA were added thereto, followed by stirring at 10° C. for 1 hour. After completion of the reaction, the reaction mixture was treated following the procedures described in Example 2 to give 2.01 g (yield 82%) of the desired compound at a high purity.

Workup

  1. customAfter completion of the reaction
  2. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-919542e266ce4fef9af84aa89e666368
Source dataset
uspto-grants-1995_09
Patent number
US05451675

Reaction notes

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