Sodium Cyanide → HCID 67160491, compound

HRID 70313Notes

Reaction equation

HRID 70313 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:10]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]=[O:32])[CH:26]=2)=[CH:21][CH:20]=1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].[CH3:33][C:34]1[CH:39]=[CH:38][C:37]([S:40]([CH2:43][N+:44]#[C-:45])(=[O:42])=[O:41])=[CH:36][CH:35]=1.[C-]#N.[Na+]>CCO.O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:10]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]3[O:32][CH:45]=[N:44][CH:43]3[S:40]([C:37]3[CH:38]=[CH:39][C:34]([CH3:33])=[CH:35][CH:36]=3)(=[O:42])=[O:41])[CH:26]=2)=[CH:23][CH:24]=1)[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 161915Tosylmethyl isocyanideHCID 866414311,1-dimethylethyl 2,3-dihydro-1H-inden-2-yl[(3'-formyl-4-biphenylyl)-methyl]carbamate

Product 1

HCID 67160491HCID 67160491, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1,1-dimethylethyl 2,3-dihydro-1H-inden-2-yl[(3′-formyl-4-biphenylyl)-methyl]carbamate (0.188 g; 0.44 mmol) and TosMIC (0.086 g; 0.44 mmol) in EtOH at room temperature was added NaCN (0.002 g; 0.04 mmol). The mixture was stirred 30 min, diluted with water and extracted with EtOAc (×3). combined organics were washed (water, brine), dried over Na2SO4 and concentrated in vacuo affording the title compound as a colorless gum, used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.35 (s, 9 H), 2.41 (s, 3 H), 2.99 (d, J=8.38 Hz, 4 H), 4.50 (br. s., 2 H), 5.65 (dd, J=5.98, 1.69 Hz, 1 H), 5.96 (d, J=5.89 Hz, 1 H), 7.07-7.18 (m, 5 H), 7.25 (partially resolved dd, J=7.85 Hz, 1 H), 7.28-7.34 (m, 2 H), 7.40 (unresolved dd, 1 H), 7.46-7.52 (m, 3 H), 7.57-7.64 (m, 2 H), 7.68 (dd, J=8.03, 1.25 Hz, 1 H), 7.74 (d, J=1.25 Hz, 1 H), 7.83-7.90 (m, 2 H).

Workup

  1. extractionextracted with EtOAc (×3)
  2. washcombined organics were washed (water, brine)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1fe00f61012485fa433aea22d91968d
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

Loading…