Boron trifluoride etherate → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

HRID 1087259Notes

Reaction equation

HRID 1087259 reaction equation
S1(CCCC1)(=O)=O.C[C:9]([O:11][CH2:12][C:13]1[CH2:22][S:21][C@@H:16]2[C@H:17]([NH2:20])[C:18](=[O:19])[N:15]2[C:14]=1[C:23]([OH:25])=[O:24])=O.B(F)(F)F.CCOCC>CO>[NH2:20][CH:17]1[C:18](=[O:19])[N:15]2[C:14]([C:23]([OH:25])=[O:24])=[C:13]([CH2:12][O:11][CH3:9])[CH2:22][S:21][C@H:16]12

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 31347SulfolaneHCID 4413287-Aminocephalosporanic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To 10 ml of sulfolane were added 1.41 g of 7-ACA, 6.3 ml of boron trifluoride ethyl ether and 2.30 ml of methanol. The mixture was heated at 50° C. for 3.5 hours to advance a reaction. 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-methoxy methyl-3-cephem-4-carboxylic acid. The amount of the desired product was 0.87 g. The yield of the desired product was 69%.

Workup

  1. customa reaction
  2. customAfter completion of the reaction

Sources & evidence

ORD record
ord-c068c3f8360e440c899e134391e8f4cc
Source dataset
uspto-grants-1991_07
Patent number
US05034521

Reaction notes

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