Methanol → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

HRID 2399843Notes

Reaction equation

HRID 2399843 reaction equation
COS(O)(=O)=O.B(OC)(OC)OC.CO.C[C:17]([O:19][CH2:20][C:21]1[CH2:30][S:29][C@@H:24]2[C@H:25]([NH2:28])[C:26](=[O:27])[N:23]2[C:22]=1[C:31]([OH:33])=[O:32])=O>O1CCOCC1>[NH2:28][CH:25]1[C:26](=[O:27])[N:23]2[C:22]([C:31]([OH:33])=[O:32])=[C:21]([CH2:20][O:19][CH3:17])[CH2:30][S:29][C@H:24]12

Participants

6

Reactant 4

HCID 887MethanolHCID 6412Monomethyl sulfateHCID 8470Trimethyl borateHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 128330237-Amino-3-methoxymethyl-3-cephem-4-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

17.94 g of a methanolic solution of methoxysulfonic acid (prepared as described in Preparation 1), 0.31 g of trimethyl borate and 2.31 g of methanol were added to 10 ml of dioxane. The mixture was cooled to 0° C., and 2.74 g of 7-ACA were added thereto, followed by stirring at 0° C. for 5 hours. After completion of the reaction, the reaction mixture was treated following the procedures described in Example 2. 2.09 g (yield 85%) of the desired compound with a high purity were thereby obtained.

Workup

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

Sources & evidence

ORD record
ord-6632c890bc4c4f5ab8b74523843f3d15
Source dataset
uspto-grants-1995_09
Patent number
US05451675

Reaction notes

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