Ethyl Acetate → HCID 86750461, compound

HRID 975691Notes

Reaction equation

[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1[CH2:32][C:33](=O)[NH2:34])=[O:6])[CH:2]=[CH2:3].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:45])=CC=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>COCCOC.O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:9][C@@H:8]1[CH2:32][C:33](=[S:45])[NH2:34])=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (2R,4S)-1-allyloxycarbonyl-2-carbamoylmethyl-4-(triphenylmethylthio) pyrrolidine (255 mg) in ethylene glycol dimethyl ether (5 ml) was added Lawesson's reagent (106 mg). After stirring at 50° C. for 4 hours, the solution was poured into a mixture of ethyl acetate and water, and adjusted to pH 7.0 with aqueous sodium hydrogen carbonate solution. The separated organic layer was washed with aqueous sodium chloride solution, dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica gel (eluent; n-hexane:ethyl acetate=2:1) to give (2R,4S)-1-allyloxycarbonyl-2-thiocarbamoylmethyl-4-(triphenyl-methylthio) pyrrolidine (130 mg).

Workup

washThe separated organic layer was washed with aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-9cfdf33ed34544d986e04e1c089a2b83
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608056

Reaction notes

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