HCID 12834136, compound → HCID 131711253, compound

HRID 851591Notes

Reaction equation

[CH2:1]([CH2:4][C:5](Cl)=[S:6])[CH:2]=[CH2:3].[CH3:8][CH:9]1[CH:14]=[C:13]([C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16])[N:12]2[C:23](=[O:26])[CH:24]([NH2:25])[C@H:11]2[S:10]1>ClCCl>[CH3:8][CH:9]1[CH:14]=[C:13]([C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:20])[Cl:21])=[O:16])[N:12]2[C:23](=[O:26])[CH:24]([NH:25][C:5](=[S:6])[CH2:4][CH2:1][CH:2]=[CH2:3])[C@H:11]2[S:10]1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of thus obtained allylthioacetyl chloride (0.452 g) in dichloromethane (3 ml) was dropwise added at -30° C. over 5 minutes to the above-mentioned solution of 2,2,2-trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate, and the mixture was stirred for 1 hour at -20° C. After the reaction, the reaction mixture was in turn washed twice with 5% hydrochloric acid, once with water, twice with a saturated sodium bicarbonate aqueous solution and once with a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. After the solvent was distilled off, the residue (0.82 g) was recrystallized from a mixture of ether and isopropyl ether to give 2,2,2-trichloroethyl 2-methyl-7-(2-allylthioacetamido)-3-cephem-4-carboxylate (0.71 g), mp 96° C.

Workup

customAfter the reaction
washwashed twice with 5% hydrochloric acid, once with water, twice with a saturated sodium bicarbonate aqueous solution and once with a saturated sodium chloride aqueous solution
dry with materialdried over magnesium sulfate
distillationAfter the solvent was distilled off
customthe residue (0.82 g) was recrystallized from a mixture of ether and isopropyl ether

Sources & evidence

ORD record: ord-33f03fd7fbe44ddd8c380e9488190183
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04385176

Reaction notes

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