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

HRID 2399838Notes

Reaction equation

HRID 2399838 reaction equation
COS(O)(=O)=O.B(OC)(OC)OC.C[C:15]([O:17][CH2:18][C:19]1[CH2:28][S:27][C@@H:22]2[C@H:23]([NH2:26])[C:24](=[O:25])[N:21]2[C:20]=1[C:29]([OH:31])=[O:30])=O>C(OC)(=O)/C=C\C(OC)=O>[NH2:26][CH:23]1[C:24](=[O:25])[N:21]2[C:20]([C:29]([OH:31])=[O:30])=[C:19]([CH2:18][O:17][CH3:15])[CH2:28][S:27][C@H:22]12

Participants

5

Reactant 3

HCID 6412Monomethyl sulfateHCID 8470Trimethyl borateHCID 4413287-Aminocephalosporanic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 5271565Dimethyl maleateSolvent

Conditions

Temperature
25 °C

Procedure

11.30 g of a methanolic solution of methoxysulfonic acid (prepared as described in Preparation 1) and 3.11 g of trimethyl borate were added to 30 ml of dimethyl maleate. The mixture was cooled to 25° C., and 2.74 g of 7-ACA were added thereto, followed by stirring at 25° C. for 1 hour. 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 at a high purity.

Workup

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

Sources & evidence

ORD record
ord-dce03295dba04b2dbd0664b6c26b70b6
Source dataset
uspto-grants-1995_09
Patent number
US05451675

Reaction notes

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