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Imidazole → 5-Pyridin-3-yl-thiophene-2-sulfonic acid {1-[2-(tert-butyl-dimethyl-silanyloxy)-5-cyano-benzyl]-2-oxo-pyrrolidin-3-(S)-yl}amide

HRID 2774
Notes
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Reaction equation

HRID 2774 reaction equation
N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].[C:14]([C:16]1[CH:17]=[CH:18][C:19]([OH:44])=[C:20]([CH:43]=1)[CH2:21][N:22]1[CH2:26][CH2:25][CH:24]([NH:27][S:28]([C:31]2[S:32][C:33]([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[CH:34][CH:35]=2)(=[O:30])=[O:29])[C:23]1=[O:42])#[N:15]>CN(C=O)C.CCOC(C)=O>[C:6]([Si:10]([CH3:13])([CH3:12])[O:44][C:19]1[CH:18]=[CH:17][C:16]([C:14]#[N:15])=[CH:43][C:20]=1[CH2:21][N:22]1[CH2:26][CH2:25][C@H:24]([NH:27][S:28]([C:31]2[S:32][C:33]([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[CH:34][CH:35]=2)(=[O:30])=[O:29])[C:23]1=[O:42])([CH3:9])([CH3:8])[CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 542646135-Pyridin-3-yl-thiophene-2-sulfonic acid {1-[5-cyano-2-hydroxy-benzyl]-2-oxo-pyrrolidin-3-yl}-amide

Product 1

HCID 542979775-Pyridin-3-yl-thiophene-2-sulfonic acid {1-[2-(tert-butyl-dimethyl-silanyloxy)-5-cyano-benzyl]-2-oxo-pyrrolidin-3-(S)-yl}amideYield 74.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

Imidazole (0.094 g, 1.37 mmol) and t-butyldimethylchlorosilane (0.099 g, 0.66 mmol) are added to a solution of 5-pyridin-3-yl-thiophene-2-sulfonic acid {1-[5-cyano-2-hydroxy-benzyl]-2-oxo-pyrrolidin-3-yl}-amide (0.25 g, 0.55 mmol) in 10 mL of DMF. The resulting mixture is stirred overnight, then diluted with EtOAc and washed with saturated NaHCO3 (aq) and brine. The organic layer is dried over MgSO4, filtered and concentrated. The product is purified by column chromatography eluting with 3% MeOH/CH2Cl2 to give a brown oil (0.236 g, 0.41 mmol).

Workup

  1. washwashed with saturated NaHCO3 (aq) and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product is purified by column chromatography
  6. washeluting with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a640257498cc4980927471255d5a0aa0
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731315

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes