Sodium hydride → HCID 15661276, compound

HRID 2249231Notes

Reaction equation

[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[O:13]([CH2:20][C:21]([NH:23][CH:24]1[C:55](=[O:56])[N:26]2[C:27]([C:39]([O:41][CH:42]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:40])=[C:28](OS(C(F)(F)F)(=O)=O)[CH2:29][S:30][C@H:25]12)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[O:13]([CH2:20][C:21]([NH:23][CH:24]1[C:55](=[O:56])[N:26]2[C:27]([C:39]([O:41][CH:42]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)=[O:40])=[C:28]([S:1][C:2]3[S:3][C:4]4[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=4[N:6]=3)[CH2:29][S:30][C@H:25]12)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 2-mercaptobenzothiazole (0.26 g. 1.54 mmol) in dry tetrahydrofuran (5.0 ml) at -78° C. was added sodium hydride (98%) (0.0369 g. 1.54 mmol). followed by diphenylmethyl 7-phenoxyacetamido-3-(trifluoromethylsulfonyloxy)-3-cephem-4-carboxylate (1.0 gm, 1.54 mmol). The reaction was warmed up to -20° C. and stirred for 16 hours before quenching in 0.5 N solution of hydrochloric acid (5 ml). The aqueous layer was extracted with dichloromethane (3×5 ml), dried (magnesium sulfate) and evaporated in vacuo to give the title compound as an oil which was purified by flash chromatography (silica, 40% ethylacetate in haxanes); yield isolated 0.7 g (70%).

Workup

custombefore quenching in 0.5 N solution of hydrochloric acid (5 ml)
extractionThe aqueous layer was extracted with dichloromethane (3×5 ml)
dry with materialdried (magnesium sulfate)
customevaporated in vacuo

Sources & evidence

ORD record: ord-6bf5135e5bee404083b1f8c66fcc3097
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05043439

Reaction notes

Loading…