Hydroxyacetonitrile → HCID 68891830, compound

HRID 1821017Notes

Reaction equation

HRID 1821017 reaction equation
[C:1](#[N:4])[CH2:2][OH:3].[C:5]([C:7]1[CH:8]=[C:9]([N:14]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:21][C:20]=3[CH3:34])[S:16][CH2:15]2)[CH:10]=[CH:11][C:12]=1F)#[N:6].[H-].[Na+]>C1COCC1.CCOC(C)=O>[C:5]([C:7]1[CH:8]=[C:9]([N:14]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])=[CH:21][C:20]=3[CH3:34])[S:16][CH2:15]2)[CH:10]=[CH:11][C:12]=1[O:3][CH2:2][C:1]#[N:4])#[N:6]

Participants

6

Reactant 3

HCID 7857HydroxyacetonitrileHCID 24758Sodium hydrideHCID 68891734HCID 68891734, compound

Product 1

HCID 68891830HCID 68891830, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

Glycolonitrile (0.013 mmol, 0.1 mL) was added to a solution of tert-butyl 3-(4-(3-(3-cyano-4-fluorophenyl)-1,3,4-thiadiazol-5-yl)-3-methylphenyl)propanoate (0.012 mmol, 0.005 g, from Step B) in THF (1 mL). Sodium hydride (95%, 5 mg) was added to the reaction mixture which was heated at 75° C. for 16 h. The reaction was diluted with EtOAc (20 mL) and washed with water (20 mL). The organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with 25% EtOAc/hexanes yielded the title compound: ESI-MS (m/z) 461.2; HPLC A: 3.94 min.

Workup

  1. washwashed with water (20 mL)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washSilica gel chromatography eluting with 25% EtOAc/hexanes

Sources & evidence

ORD record
ord-9278d114321c4e24a48053116f44a516
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

Loading…