Ethyl Acetate → (2S,4R)-2-(2-aminothiazol-4-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
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.[NH2:28][C:29]([NH2:31])=[S:30].C(OCC)(=O)C>CO.ClCCl>[NH2:31][C:29]1[S:30][CH:2]=[C:3]([C@@H:5]2[CH2:9][C@@H:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:7][N:6]2[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[N:28]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (660 mg) in a mixture of methanol (20 ml) and dichloromethane (20 ml) was added thiourea (165 mg) at room temperature. After stirring at the same temperature for 3 hours, the mixture was poured into ethyl acetate, washed in turn with saturated aqueous sodium bicarbonate and brine. The dried organic layer was evaporated, and the resulting oil was crystallized from a mixture of n-hexane and methanol (100:1 V/V) to give (2S,4R)-2-(2-aminothiazol-4-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (550 mg).
Workup
- washwashed in turn with saturated aqueous sodium bicarbonate and brine
- customThe dried organic layer was evaporated
- customthe resulting oil was crystallized from a mixture of n-hexane and methanol (100:1 V/V)
Sources & evidence
- ORD record
- ord-8d8883749bb84755baa0892e824c04f6
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04921852
Reaction notes
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