Ethyl Acetate → HCID 57256090, compound

HRID 37252Notes

Reaction equation

Br[CH2:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:7][N:6]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:16])=O.[N+:28]([C:31]1[CH:45]=[CH:44][C:34]([CH2:35][O:36][C:37]([NH:39][CH2:40][C:41]([NH2:43])=[S:42])=[O:38])=[CH:33][CH:32]=1)([O-:30])=[O:29].C(OCC)(=O)C>CO.ClCCl>[CH3:14][S:11]([O:10][C@H:8]1[CH2:7][N:6]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[O:16])[C@H:5]([C:3]2[N:43]=[C:41]([CH2:40][NH:39][C:37]([O:36][CH2:35][C:34]3[CH:44]=[CH:45][C:31]([N+:28]([O-:30])=[O:29])=[CH:32][CH:33]=3)=[O:38])[S:42][CH:2]=2)[CH2:9]1)(=[O:13])=[O:12]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (2S, 4R) -2-bromoacetyl-4-methanesulfonyloxy-1- (4-nitrobenzyloxycarbonyl)pyrrolidine (840 mg) in a mixture of methanol (30 ml) and dichloromethane (20 ml) was added 2-(4-nitrobenzyloxycarbonylamino)thioacetamide (700 mg) at room temperature. After stirring at 60° C. for 2 hours, the mixture was poured into ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine successively. The dried organic layer was evaporated and the resulting oil was subjected to a column chromatography on silica gel (30 g) eluting with ethyl acetate to give (2S, 4R) -4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) -2- [2-{N-(4-nitrobenzyloxycarbonyl) aminomethyl}-thiazol-4-yl]pyrrolidine (540 mg).

Workup

washwashed with saturated aqueous sodium bicarbonate and brine successively
customThe dried organic layer was evaporated
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-014a53d1ae1d429e9c348b79eafe0e92
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420122

Reaction notes

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