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

HRID 2399840Notes

Reaction equation

HRID 2399840 reaction equation
COS(O)(=O)=O.B(OC)(OC)OC.S1(CCCC1)(=O)=O.C[C:22]([O:24][CH2:25][C:26]1[CH2:35][S:34][C@@H:29]2[C@H:30]([NH2:33])[C:31](=[O:32])[N:28]2[C:27]=1[C:36]([OH:38])=[O:37])=O>>[NH2:33][CH:30]1[C:31](=[O:32])[N:28]2[C:27]([C:36]([OH:38])=[O:37])=[C:26]([CH2:25][O:24][CH3:22])[CH2:35][S:34][C@H:29]12

Participants

5

Reactant 4

HCID 6412Monomethyl sulfateHCID 8470Trimethyl borateHCID 31347SulfolaneHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 128330237-Amino-3-methoxymethyl-3-cephem-4-carboxylic acidYield 88%

Conditions

Temperature
15 °C

Procedure

11.9 g of a methanolic solution of methoxysulfonic acid (prepared as described in Preparation 2) and 2.10 g of trimethyl borate were added to 15 ml of sulfolane. 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 hour. After completion of the reaction, the reaction mixture was treated following the procedures described in Example 2 to give 2.16 g (yield 88%) 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-064647b7c2464991a7d3d774e5d91075
Source dataset
uspto-grants-1995_09
Patent number
US05451675

Reaction notes

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