Water → HCID 135767960, compound

HRID 1755841Notes

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.[SH:19][C:20]1[N:25]2[N:26]=[CH:27][CH:28]=[C:24]2[N:23]=[C:22]([C:29]2[CH:30]=[C:31]([OH:36])[C:32](=[CH:34][CH:35]=2)[OH:33])[CH:21]=1.B(F)(F)F.CCOCC.O>S1(CCCC1)(=O)=O.ClCCl>[NH2:13][C@@H:10]1[C:11](=[O:12])[N:8]2[C@@H:9]1[S:14][CH2:15][C:6]([CH2:5][S:19][C:20]1[N:25]3[N:26]=[CH:27][CH:28]=[C:24]3[N:23]=[C:22]([C:29]3[CH:35]=[CH:34][C:32]([OH:33])=[C:31]([OH:36])[CH:30]=3)[CH:21]=1)=[C:7]2[C:16]([OH:18])=[O:17]

Participants

Conditions

Temperature: 25 °C

Procedure

7-Aminocephalosporanic acid (272 mg) and 272 mg of the above 4-(7-mercaptopyrazolo[1,5-a]pyrimidin-5-yl)pyrocatechol are suspended in a mixture of 2 ml of sulpholane and 2 ml of dichloromethane. 0.75 ml of boron trifluoride etherate is added thereto and the mixture is stirred at 25° C. for 5 hours. Thereafter, it is treated with 20 ml of water, the aqueous phase is separated, its pH is adjusted to 3.5 using concentrated aqueous amonia solution and the precipitated product is filtered off under suction, washed with water, methanol and finally with diethyl ether and dried at 0.1 mmHg and 40° C. There are obtained 350 mg of (6R,7R)-7-amino-3-[[[5-(3,4-dihydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Workup

customthe aqueous phase is separated
filtrationthe precipitated product is filtered off under suction
washwashed with water, methanol and finally with diethyl ether
customdried at 0.1 mmHg and 40° C

Sources & evidence

ORD record: ord-b557b20465564761ba1e49d760d9a468
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438052

Reaction notes

Loading…