Water → (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-[5-(4-nitrobenzyloxycarbonylamino)-1,3-dioxan-2-yl]pyrrolidine

HRID 37269

Reaction equation

HRID 37269 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][O:9][C:10]([NH:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:20]([S:23][C@@H:24]1[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[C@H:26]([CH:42]=O)[CH2:25]1)(=[O:22])[CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:20]([S:23][C@@H:24]1[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[C@H:26]([CH:42]2[O:17][CH2:16][CH:13]([NH:12][C:10]([O:9][CH2:8][C:7]3[CH:18]=[CH:19][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[O:11])[CH2:14][O:15]2)[CH2:25]1)(=[O:22])[CH3:21]

Participants

7

Reactant 4

HCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 18638815(2S,4S)-4-acetylthio-2-formyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidineHCID 199345222-(4-Nitrobenzyloxycarbonyl)amino-1,3-propanediol

Product 1

HCID 18638810(2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-[5-(4-nitrobenzyloxycarbonylamino)-1,3-dioxan-2-yl]pyrrolidineYield 85.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-nitrobenzyloxycarbonyl)amino-1,3-propanediol (1.42 g), (2S,4S)-4-acetylthio-2-formyl-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (1.00 g) and 4-toluene-sulfonic acid (0.30 g) in toluene was refluxed for 2 hours with removing water under azeotropic condition. The reaction mixture was poured into a mixture of water and ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (80 ml) and eluted with a mixture of acetone and dichloromethane (1:9, V/V) to give (2S, 4S)-4-acetylthio-1- (4-nitrobenzyloxycarbonyl)-2-[5-(4-nitrobenzyloxycarbonylamino) -1,3-dioxan-2-yl]pyrrolidine (1.47 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (80 ml)
  6. washeluted with a mixture of acetone and dichloromethane (1:9, V/V)

Sources & evidence

ORD record
ord-ae36b222e23a4aec9fa43903c97c4233
Source dataset
uspto-grants-1995_05
Patent number
US05420122

Linked notes

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