Ammonia → 7-Amino-3-[(2-hydroxymethyl-5-methyl-s-triazolo[1,5-a]pyrimidin7-yl)thiomethyl]-3-cephem-4-carboxylic acid
Reaction equation
[OH:1][CH2:2][C:3]1[N:13]=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([SH:11])[N:5]2[N:4]=1.CC(O[CH2:18][C:19]1[CH2:28][S:27][C@@H:22]2[C@H:23]([NH2:26])[C:24](=[O:25])[N:21]2[C:20]=1[C:29]([OH:31])=[O:30])=O.O.N>C(#N)C>[NH2:26][CH:23]1[C:24](=[O:25])[N:21]2[C:20]([C:29]([OH:31])=[O:30])=[C:19]([CH2:18][S:11][C:10]3[N:5]4[N:4]=[C:3]([CH2:2][OH:1])[N:13]=[C:6]4[N:7]=[C:8]([CH3:12])[CH:9]=3)[CH2:28][S:27][C@H:22]12Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
In 130 ml of acetonitrile were suspended 11.08 g of 2- hydroxymethyl-7-mercapto-5-methyl-s-triazolo[1,5-a]pyrimidine and 15.38 g of 7-aminocephalosporanic acid, and 24.6 ml of boron trifluoride-ethy: ether complex was added thereto and the mixture was stirred at 50° C. for 2 hours. After the reaction mixture was ice-cooled, 300 ml of water was added thereto and pH thereof was adjusted to 2 with conc. aqueous ammonia. The precipitated crystals were collected by filtration, washed with water and with acetone, and then dried to obtain 18.5 of the title compound.
Workup
- additionether complex was added
- temperaturecooled
- filtrationThe precipitated crystals were collected by filtration
- washwashed with water and with acetone
- customdried
Sources & evidence
- ORD record
- ord-db4e7290558745e29394a69f38020ef5
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04958019
Reaction notes
Loading…