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

HRID 2399845Notes

Reaction equation

HRID 2399845 reaction equation
COS(O)(=O)=O.COCOC.C[C:13]([O:15][CH2:16][C:17]1[CH2:26][S:25][C@@H:20]2[C@H:21]([NH2:24])[C:22](=[O:23])[N:19]2[C:18]=1[C:27]([OH:29])=[O:28])=O>C(OC)(=O)CCC(OC)=O>[NH2:24][CH:21]1[C:22](=[O:23])[N:19]2[C:18]([C:27]([OH:29])=[O:28])=[C:17]([CH2:16][O:15][CH3:13])[CH2:26][S:25][C@H:20]12

Participants

5

Reactant 3

HCID 6412Monomethyl sulfateHCID 8020DimethoxymethaneHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 128330237-Amino-3-methoxymethyl-3-cephem-4-carboxylic acidYield 83%

Reagents, catalysts & solvents 1

HCID 7820Dimethyl SuccinateSolvent

Conditions

Temperature
15 °C

Procedure

17.94 g of a methanolic solution of methoxysulfonic acid (prepared as described in Preparation 1) and 6.12 g of methylal (prepared as described in Preparation 5) were added to 30 ml of dimethyl succinate. The mixture was cooled to 15° C., and 2.74 g of 7-ACA were added thereto, followed by stirring at 15° C. for 1.5 hours. After completion of the reaction, the reaction mixture was treated following the procedures described in Example 2 to give 2.04 g (yield 83%) of the desired compound with a high purity.

Workup

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

Sources & evidence

ORD record
ord-4e5b3de71cd74ec180dc119ae6381f64
Source dataset
uspto-grants-1995_09
Patent number
US05451675

Reaction notes

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