Ammonia → HCID 135996344, compound
Reaction equation
C(#N)C.CC(O[CH2:8][C:9]1[CH2:18][S:17][C@@H:12]2[C@H:13]([NH2:16])[C:14](=[O:15])[N:11]2[C:10]=1[C:19]([OH:21])=[O:20])=O.[SH:22][C:23]1[O:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([OH:35])[CH:29]=2)=[N:26][N:27]=1.B(F)(F)F.CCOCC.N>O>[NH2:16][C@@H:13]1[C:14](=[O:15])[N:11]2[C:10]([C:19]([OH:21])=[O:20])=[C:9]([CH2:8][S:22][C:23]3[O:24][C:25]([C:28]4[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([OH:35])[CH:29]=4)=[N:26][N:27]=3)[CH2:18][S:17][C@H:12]12Participants
7
Conditions
- Temperature
- 50 °C
Procedure
To 520 ml of acetonitrile 16.3 g (60 mmol) of 7β-aminocephalosporanic acid and 13.9 g (66 mmol) of 2-mercapto-5-(3,4-dihydroxyphenyl)-1,3,4-oxadiazole and 45.4 ml (360 mmol) of boron trifluoride diethyl etherate were added, and stirred at 50° C. for 3 hours. The reaction solution was cooled and poured into 450 ml of cold water. The mixture was stirred at room temperature for 1 hour and adjusted to pH2.0 with a 25% aqueous ammonia. The mixture was stirred at not more than 5° C. for 1 hour, and the precipitates were collected by filtration. The precipitates were washed with water and ethyl acetate and dried to obtain 21.3 g (yield: 84.1%) of the above identified compound.
Workup
- temperatureThe reaction solution was cooled
- stirringThe mixture was stirred at room temperature for 1 hour
- stirringThe mixture was stirred at not more than 5° C. for 1 hour
- filtrationthe precipitates were collected by filtration
- washThe precipitates were washed with water and ethyl acetate
- customdried
- customto obtain 21.3 g (yield: 84.1%) of the
Sources & evidence
- ORD record
- ord-de7d9cd65d184be89f6a471f4ff12a87
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05061794
Reaction notes
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