Water → HCID 86705552, compound

HRID 2279567Notes

Reaction equation

HRID 2279567 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10][CH2:11]I)[CH:5]=[CH:6][C:7]=1[Cl:8].[C-:21]#[N:22].[Na+].O>CS(C)=O>[C:21]([CH2:11][CH2:10][C@@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)#[N:22]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 86705551HCID 86705551, compound

Product 1

HCID 86705552HCID 86705552, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 366 (810 mg, 1.88 mmol) in DMSO (4 mL) at RT was added NaCN (102 mg, 2.07 mmol) and the resulting mixture was stirred at 80° C. overnight. The mixture was poured into water, extracted with EtOAc, washed with brine, dried (MgSO4), and concentrated. The product was purified by SiO2 chromatography eluting with 20% EtOAc/hexanes to afford 534 mgs (86%) of (R)-tert-butyl 3-cyano-1-(3,4-dichlorophenyl)propylcarbamate (368).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe product was purified by SiO2 chromatography
  6. washeluting with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-4427b84bea63491d9f5c3af5913fcc2e
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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