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

HRID 2399842Notes

Reaction equation

HRID 2399842 reaction equation
B(OC)(OC)OC.COS(O)(=O)=O.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>>[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

4

Reactant 3

HCID 6412Monomethyl sulfateHCID 8470Trimethyl borateHCID 4413287-Aminocephalosporanic acid

Product 1

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

Conditions

Temperature
-5 °C

Procedure

15.80 g of trimethyl borate were added to 17.9 g of a methanolic solution of methoxysulfonic acid (prepared as described in Preparation 2). The mixture was cooled to -5° C., and 2.74 g of 7-ACA were added thereto, followed by stirring at -5° C. for 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 in a highly pure form.

Workup

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

Sources & evidence

ORD record
ord-01639b0eca114721be405f89f0a35241
Source dataset
uspto-grants-1995_09
Patent number
US05451675

Reaction notes

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