Boron trifluoride etherate → 7-amino-3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

HRID 1577747Notes

Reaction equation

HRID 1577747 reaction equation
CC(O[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.[C:19]([CH2:22][CH2:23][N:24]1[C:28]([SH:29])=[N:27][N:26]=[N:25]1)([OH:21])=[O:20].B(F)(F)F.CCOCC>C(#N)C>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:29][C:28]3[N:24]([CH2:23][CH2:22][C:19]([OH:21])=[O:20])[N:25]=[N:26][N:27]=3)[CH2:15][S:14][C@H:9]12

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 178525591HCID 178525591, compound

Product 1

HCID 705155727-amino-3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acidYield 80.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-aminocephalosporanic acid (38.4 g) and 1-(2-carboxyethyl)-1H-tetrazole-5-thiol (20.0 g) were reacted in the presence of boron trifluoride etherate (80.0 g) and dry acetonitrile (200 ml) to give 7-amino-3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (35.52 g).

Sources & evidence

ORD record
ord-ea3a970539704767b65b2a7d9238457a
Source dataset
uspto-grants-1981_09
Patent number
US04288436

Reaction notes

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