Ethyl Acetate → (2S,4R)-2-[2-(N-t-butoxycarbonylamino) methylthiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37278Notes

Reaction equation

HRID 37278 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.[C:28]([O:32][C:33]([NH:35][CH2:36][C:37]([NH2:39])=[S:38])=[O:34])([CH3:31])([CH3:30])[CH3:29].C(OCC)(=O)C>CO.ClCCl>[C:28]([O:32][C:33]([NH:35][CH2:36][C:37]1[S:38][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:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[O:16])[N:39]=1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 5324304tert-butyl N-(carbamothioylmethyl)carbamateHCID 14305067(2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 57303896(2S,4R)-2-[2-(N-t-butoxycarbonylamino) methylthiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 40.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S, 4R)-2-bromoacetyl-4-methanesulfonyloxy-1- (4-nitrobenzyloxycarbonyl)pyrrolidine (20 g) in a mixture of methanol (200 ml) and dichloromethane (200 ml) was added 2-(N-t-butoxycarbonylamino)thioacetamide (20 g) at room temperature. After stirring at ambient temperature for 12 hours, the mixture was poured into ethyl acetate, washed with saturated sodium bicarbonate and brine successively. The dried organic layer was evaporated, and the obtained oil was subjected to a column chromatography on silica gel and eluted with a mixture of acetone and dichloromethane (1:5, V/V) to give (2S,4R)-2-[2-(N-t-butoxycarbonylamino) methylthiazol-4-yl]-4-methanesulfonyloxy-1- (4-nitrobenzyloxycarbonyl)pyrrolidine (9.7 g).

Workup

  1. washwashed with saturated sodium bicarbonate and brine successively
  2. customThe dried organic layer was evaporated
  3. washeluted with a mixture of acetone and dichloromethane (1:5, V/V)

Sources & evidence

ORD record
ord-70e627ccace2495b9196189cc6592f0f
Source dataset
uspto-grants-1995_05
Patent number
US05420122

Reaction notes

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