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

HRID 2399847Notes

Reaction equation

HRID 2399847 reaction equation
COS(O)(=O)=O.B(OC)(OC)OC.COCOC.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 8020DimethoxymethaneHCID 8470Trimethyl borateHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 128330237-Amino-3-methoxymethyl-3-cephem-4-carboxylic acidYield 79%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
10 °C

Procedure

16.7 g of a methanolic solution of methoxysulfonic acid (prepared as described in Preparation 2), 2.18 g of trimethyl borate and 2.45 g of methylal (prepared as described in Preparation 5) were added to 20 ml of sulfolane. The mixture was cooled to 10° C., and 2.74 g of 7-ACA were added thereto, followed by stirring at 10° C. for 1.5 hours. After completion of the reaction, the reaction mixture was treated following the procedures described in Example 2. 1.94 g (yield 79%) of the title compound were produced with high purity.

Workup

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

Sources & evidence

ORD record
ord-ec5ce55f3d294bf08a7d9a69698cc705
Source dataset
uspto-grants-1995_09
Patent number
US05451675

Reaction notes

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