Methanesulfonic Acid → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

HRID 1087246Notes

Reaction equation

HRID 1087246 reaction equation
C[C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.CS(O)(=O)=O.B(OC)(OC)OC>ClCCl>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][O:4][CH3:2])[CH2:15][S:14][C@H:9]12

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8470Trimethyl borateHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 128330237-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 10 ml of dichloromethane were added 1.41 g of 7-ACA, 5.1 ml of methanesulfonic acid and 1.07 ml of trimethyl borate. The reaction was conducted at 0° C. for 9 hours. After completion of the reaction, substantially the same procedure as in Example 1 was repeated, to thereby obtain the desired product, namely 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 0.70 g. The yield of the desired product was 55%.

Workup

  1. customAfter completion of the reaction

Sources & evidence

ORD record
ord-dba9f4a0ecbc449b92c5887351e1036b
Source dataset
uspto-grants-1991_07
Patent number
US05034521

Reaction notes

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