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

HRID 2399839Notes

Reaction equation

HRID 2399839 reaction equation
COS(O)(=O)=O.B(OC)(OC)OC.C(=O)(OC)OC.C(OC)(=O)C.C[C:26]([O:28][CH2:29][C:30]1[CH2:39][S:38][C@@H:33]2[C@H:34]([NH2:37])[C:35](=[O:36])[N:32]2[C:31]=1[C:40]([OH:42])=[O:41])=O>>[NH2:37][CH:34]1[C:35](=[O:36])[N:32]2[C:31]([C:40]([OH:42])=[O:41])=[C:30]([CH2:29][O:28][CH3:26])[CH2:39][S:38][C@H:33]12

Participants

6

Reactant 5

HCID 6412Monomethyl sulfateHCID 6584Methyl AcetateHCID 8470Trimethyl borateHCID 12021Dimethyl CarbonateHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 128330237-Amino-3-methoxymethyl-3-cephem-4-carboxylic acidYield 84%

Conditions

Temperature
20 °C

Procedure

11.9 g of a methanolic solution of methoxysulfonic acid (prepared as described in Preparation 2) and 3.11 g of trimethyl borate were added to a mixture of 25 ml of dimethyl carbonate and 5 ml of methyl acetate. The mixture was cooled to 20° C., and 2.74 g of 7-ACA were added thereto, followed by stirring at 20° C. for 1 hour. After completion of the reaction, the reaction mixture was treated following the procedures described in Example 2. 2.06 g (yield 84%) of the title compound in a highly pure form were produced.

Workup

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

Sources & evidence

ORD record
ord-0d29ef4df8fb45928b1b85d2ac9197d7
Source dataset
uspto-grants-1995_09
Patent number
US05451675

Reaction notes

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