Imidazole → N-Allyl-N-{2-[3-(S)-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-1-yl]-2-oxo-1-(S)-phenyl-ethyl}-2-nitro-benzenesulfonamide

HRID 23585Notes

Reaction equation

HRID 23585 reaction equation
[CH2:1]([N:4]([C@@H:17]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:18]([N:20]1[CH2:24][CH2:23][C@H:22]([OH:25])[CH2:21]1)=[O:19])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6])[CH:2]=[CH2:3].N1C=CN=C1.[Si:37](Cl)([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38].O>CN(C)C=O>[CH2:1]([N:4]([C@@H:17]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:18]([N:20]1[CH2:24][CH2:23][C@H:22]([O:25][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH2:21]1)=[O:19])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:6])=[O:7])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 20756543N-Allyl-N-[2-(3-(S)-hydroxy-pyrrolidin-1-yl)-2-oxo-1-(S)-phenyl-ethyl]-2-nitro-benzenesulfonamide

Product 1

HCID 20756544N-Allyl-N-{2-[3-(S)-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-1-yl]-2-oxo-1-(S)-phenyl-ethyl}-2-nitro-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution N-allyl-N-[2-(3-(S)-hydroxy-pyrrolidin-1-yl)-2-oxo-1-(S)-phenyl-ethyl]-2-nitro-benzenesulfonamide (7.13 g, 16.0 mmol) in anhydrous dimethylformamide (16 cm3) was added imidazole (2.18 g, 32.0 mmol). When the imidazole dissolved tert-butyldimethylsilyl chloride was added and stirred at ambient temperature for 3 hours. The solution was poured into water (200 cm3), extracted with ethyl ether (3×50 cm3), washed with water (2×40 cm3), brine (40 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a yellow glass (8.73 g, 97.4%) with a positive ion ESI (M+H)+560.3

Workup

  1. additionwas added
  2. extractionextracted with ethyl ether (3×50 cm3)
  3. washwashed with water (2×40 cm3), brine (40 cm3)
  4. dry with materialdried over sodium sulfate, vacuum
  5. filtrationfiltered
  6. customthe volatile fractions removed in vacuo to a yellow glass (8.73 g, 97.4%) with a positive ion ESI (M+H)+560.3

Sources & evidence

ORD record
ord-da08ae8ff8114830a09c70041522da9c
Source dataset
uspto-grants-2005_02
Patent number
US06852713B2

Reaction notes

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