Sodium Cyanide → (2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(cyanomethyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627193Notes

Reaction equation

HRID 627193 reaction equation
[C-:1]#[N:2].[Na+].[CH2:4]([O:7][N:8]([CH:21]1[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:24]([CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH:23]=[C:22]1[CH2:43]OS(C)(=O)=O)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[CH:5]=[CH2:6]>O.CN(C=O)C.C([O-])(O)=O.[Na+]>[CH2:4]([O:7][N:8]([CH:21]1[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C@H:24]([CH2:34][O:35][Si:36]([C:39]([CH3:40])([CH3:41])[CH3:42])([CH3:38])[CH3:37])[CH:23]=[C:22]1[CH2:43][C:1]#[N:2])[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:10])=[O:11])[CH:5]=[CH2:6]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 89851930(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(((methylsulfonyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 89851795(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(cyanomethyl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of sodium cyanide (4.94 g, 100.85 mmol) in water (20.0 mL) was added (2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(((methylsulfonyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate (crude, 20.17 mmol) in DMF (100 mL). The mixture was then stirred at room temperature for 15 h. It became a dark orange solution. It was then diluted with sat. NaHCO3 and water and extracted with ethyl acetate, dried over MgSO4. The crude was subjected to silica gel column eluting with 0-100% ethyl acetate/hexanes to give a pale yellow oil, 5.92 g, 47.1%.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. washeluting with 0-100% ethyl acetate/hexanes
  4. customto give a pale yellow oil, 5.92 g, 47.1%

Sources & evidence

ORD record
ord-65868645541147c1bf86ab5168c095e9
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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