HCID 57077698, compound → HCID 57060281, compound

HRID 1590474Notes

Reaction equation

HRID 1590474 reaction equation
C(OC([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C@@H:15]2[CH2:19][C@H:18]([S:20][C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][N:16]2[C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][CH:45]=2)=[O:41])[CH2:10]1)=O)(C)(C)C>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.C(OCC)(=O)C>[NH2:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C@@H:15]2[CH2:19][C@H:18]([S:20][C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:17][N:16]2[C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][CH:45]=2)=[O:41])[CH2:10]1

Participants

5

Reactant 1

HCID 57077698HCID 57077698, compound

Product 1

HCID 57060281HCID 57060281, compound

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2S,4S)-2-[(3S)-3-t-butoxycarbonylaminopyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (2.14 g) in a mixture of trifluoroacetic acid (10 ml) and anisole (1 ml) was stirred on ice-bath for 1 hour. The reaction mixture was evaporated in vacuo to give a residue. The residue was dissolved in ethyl acetate (100 ml) and the solution was washed with saturated aqueous sodium hydrogen carbonate (50 ml) and saturated aqueous sodium chloride, dried over magnesium sulfate, and evaporated in vacuo to give a residue of (2S,4S)-2-[(3S)-3-aminopyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine. To a solution of the residue in a mixture of ethyl acetate (40 ml) and water (20 ml) was dropwise added a soluiton of 4-nitrobenzyloxycarbonyl chloride (1.06 g) in tetrahydrofuran (10 ml) under ice-cooling, keeping the pH between 8 and 9 with 1N aqueous sodium hydroxide solution. The mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added ethyl acetate (50 ml). The solution was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (100 g) eluting with a mixture of dichloromethane and acetone (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-[(3S)-3-(4-nitrobenzyloxycarbonylamino)pyrrolidin-1-yl]methyl-4-(triphenylmethylthio)pyrrolidine (1.89 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto give a residue
  3. washthe solution was washed with saturated aqueous sodium hydrogen carbonate (50 ml) and saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-6703c381d30e415d94c29f64457aeb5e
Source dataset
uspto-grants-1993_04
Patent number
US05202437

Reaction notes

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