Trityl chloride → (4-Nitrophenyl)methyl (2S,4S)-2-cyano-4-[(triphenylmethyl)sulfanyl]pyrrolidine-1-carboxylate

HRID 37265Notes

Reaction equation

HRID 37265 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([C:23]#[N:24])[CH2:6]1)(=O)C.C[O-].[Na+].[C:28](Cl)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO.O1CCCC1.C(OCC)(=O)C>[C:23]([C@@H:7]1[CH2:6][C@H:5]([S:4][C:28]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:9][N:8]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:11])#[N:24]

Participants

7

Reactant 3

HCID 6456Trityl chlorideHCID 10942334Sodium MethoxideHCID 57287687HCID 57287687, compound

Product 1

HCID 53487023(4-Nitrophenyl)methyl (2S,4S)-2-cyano-4-[(triphenylmethyl)sulfanyl]pyrrolidine-1-carboxylateYield 59.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (2S ,4S)-4-acetylthio-2-cyano-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (2.60 g) in a mixture of methanol (26 ml) and tetrahydrofuran (52 ml) was added a 28% solution of sodium methoxide in methanol (1.8 ml) at -10°∫-5° C. and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added trityl chloride (2.20 g) at -10°∫-5° C., followed by stirring at the same temperature for 1 hour. The mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (40 g) and eluted with dichloromethane to give (2S,4S)-2-cyano-1-(4-nitrobenzyloxycarbonyl) -4-tritylthiopyrrolidine (2.45 g).

Workup

  1. stirringby stirring at the same temperature for 1 hour
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give a residue
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a syrup
  8. washeluted with dichloromethane

Sources & evidence

ORD record
ord-270db159db954f6a913af0612c991d81
Source dataset
uspto-grants-1995_05
Patent number
US05420122

Reaction notes

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