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

HRID 2399841Notes

Reaction equation

HRID 2399841 reaction equation
COS(O)(=O)=O.B(OC)(OC)OC.C(OC)(=O)C.C[C:20]([O:22][CH2:23][C:24]1[CH2:33][S:32][C@@H:27]2[C@H:28]([NH2:31])[C:29](=[O:30])[N:26]2[C:25]=1[C:34]([OH:36])=[O:35])=O>S1(CCCC1)(=O)=O>[NH2:31][CH:28]1[C:29](=[O:30])[N:26]2[C:25]([C:34]([OH:36])=[O:35])=[C:24]([CH2:23][O:22][CH3:20])[CH2:33][S:32][C@H:27]12

Participants

6

Reactant 4

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

Product 1

HCID 128330237-Amino-3-methoxymethyl-3-cephem-4-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
20 °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 a solution containing 10 ml of sulfolane 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 to give 2.11 g (yield 86%) 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-207ddd7570c545a39c46e81f7e115b1e
Source dataset
uspto-grants-1995_09
Patent number
US05451675

Reaction notes

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