Phosphorus oxychloride → HCID 86756325, compound

HRID 568284Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.[C:6]([S:9][C@H:10]1[CH2:14][C@@H:13]([C:15]([NH:17][CH2:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=O)[N:12]([C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])[CH2:11]1)(=[O:8])[CH3:7]>C1(C)C=CC=CC=1>[C:6]([S:9][C@H:10]1[CH2:14][CH:13]([C:15]2[N:23]3[C:19]([S:20][CH:21]=[CH:22]3)=[CH:18][N:17]=2)[N:12]([C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])[CH2:11]1)(=[O:8])[CH3:7]

Participants

Conditions

Temperature: 100 °C

Procedure

Phosphorus oxychloride (1.2 ml) is added to a solution of 1.00 g of (3S,5S)-3-acetylthio-1-allyloxycarbonyl-5-[(thiazol-2-yl)methylaminocarbonyl]pyrrolidine in 10 ml of toluene, and the mixture is stirred at 100° C. for one hr. The reaction mixture is concentrated under reduced pressure, dichloromethane is added to the residue, and the mixture is successively washed with an aqueous potassium carbonate solution and saturated saline and dried over magnesium sulfate. The solvent is removed by evaporation, and the residue is purified by column chromatography on silica gel to give 0.27 g of the title compound (stereoisomer A: a high polar component) and 0.07 g of the title compound (stereoisomer B: a low polar component).

Workup

concentrationThe reaction mixture is concentrated under reduced pressure, dichloromethane
additionis added to the residue
washthe mixture is successively washed with an aqueous potassium carbonate solution and saturated saline
dry with materialdried over magnesium sulfate
customThe solvent is removed by evaporation
customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-def94d8b524a410f856930b712af333e
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180622B2

Reaction notes

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