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

HRID 1087257Notes

Reaction equation

HRID 1087257 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.B(F)(F)F.CCOCC.FS(O)(=O)=O.B(OC)(OC)OC>S1(CCCC1)(=O)=O>[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

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8470Trimethyl borateHCID 24603Fluorosulfuric acidHCID 4413287-Aminocephalosporanic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
25 °C

Procedure

To 20 ml of sulfolane were added 1.41 g of 7-ACA, 8.2 ml of boron trifluoride ethyl ether, 1.9 ml of fluorosulfonic acid and 6.12 ml of trimethyl borate. The mixture was heated at 25° C. for 20 minutes 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-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 0.76 g. The yield of the desired product was 60%.

Workup

  1. customa reaction
  2. customAfter completion of the reaction

Sources & evidence

ORD record
ord-cd2a5c67c1404001a11a7e2cc0b354e9
Source dataset
uspto-grants-1991_07
Patent number
US05034521

Reaction notes

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