Dimethylformamide → (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-(4-sulfamoylphenyl)thiomethylpyrrolidine

HRID 725940Notes

Reaction equation

HRID 725940 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[SH:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH2:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1.CN(C)C=O.C1CCN2C(=NCCC2)CC1>C1COCC1.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:15])[CH3:16])[CH2:10][C@H:9]1[CH2:21][S:27][C:28]1[CH:29]=[CH:30][C:31]([S:34](=[O:36])(=[O:35])[NH2:37])=[CH:32][CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 116503Benzenesulfonamide, 4-mercapto-HCID 14117008(2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 22881073(2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-(4-sulfamoylphenyl)thiomethylpyrrolidineYield 43.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a liquid mixture of a solution of (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-mesyloxymethylpyrrolidine (5.02 g, 12.3 mmol) and p-mercaptobenzenesulfonamide (2.39 g, 12.6 mmol) in THF (60 ml) with -N,N-dimethylformamide (20 ml), 1,8-diazabicyclo[5.4.0]-7-undecene (2.46 ml, 16.4 ml) was added dropwise in a nitrogen stream at room temperature. The reaction solution was stirred at the same temperature for 7 hours and then poured into a liquid mixture of ethyl acetate with water. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and then concentrated in vacuo. The resulting residue was subjected to silica gel column chromatography (Wakogel™ C-300 heptane-ethyl acetate 9:1→4:1→3:2) to give (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-(4-sulfamoylphenyl)thiomethylpyrrolidine (2.65 g, yield: 43.1%) as a colorless oily substance.

Workup

  1. additionwas added dropwise in a nitrogen stream at room temperature
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09264d9960644eab95f0b55974493a53
Source dataset
uspto-grants-1998_01
Patent number
US05707987

Reaction notes

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