1-Butanol → HCID 70583915, compound

HRID 2052178Notes

Reaction equation

P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.S1C=CC=C1CC([NH:21][CH:22]1[C:54](=[O:55])[N:24]2[C:25]([C:38]([O:40][CH:41]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:39])=[C:26]([C:29]3[S:30][C:31]([NH:34][C:35](=[O:37])[CH3:36])=[N:32][N:33]=3)[CH2:27][S:28][C@H:23]12)=O.C(O)CCC>ClCCl>[NH2:21][CH:22]1[C:54](=[O:55])[N:24]2[C:25]([C:38]([O:40][CH:41]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:39])=[C:26]([C:29]3[S:30][C:31]([NH:34][C:35](=[O:37])[CH3:36])=[N:32][N:33]=3)[CH2:27][S:28][C@H:23]12

Participants

Conditions

Temperature: -40 °C

Procedure

To a suspension of 1.5 g of phosphorous pentachloride in 13 ml of dichloromethane is added 1.2 g of pyridine in 13 ml of dichloromethane under stirring at -40° C. To the resulting mixture is added 1.6 g of benzhydryl 7-thienylacetamido-3-(5-acetylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylate in 32 ml of dichloromethane at -40° C. After stirring for one hour at 0° C., to the reaction mixture is added 6 g of n-butanol under stirring at -40° C. After working up as described in Example 26, the obtained residue is chromatographed on a column of silica gel [eluting with ethyl acetate-dichloromethane (1:1)] to give 0.522 g of benzhydryl 7-amino-3-(5-acetylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylate as pale yellow needles.

Workup

stirringAfter stirring for one hour at 0° C., to the reaction mixture
stirringunder stirring at -40° C
customthe obtained residue is chromatographed on a column of silica gel [eluting with ethyl acetate-dichloromethane (1:1)]

Sources & evidence

ORD record: ord-38c9442531524d2e9316e38859e7fbfb
Source dataset: uspto-grants-1980_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04182866

Reaction notes

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