Sodium Chloride → HCID 59161750, compound

HRID 409414Notes

Reaction equation

HRID 409414 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][CH:14]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)(=O)=O)=CC=1.[C-]#[N:29].[Na+].[Na+].[Cl-]>CS(C)=O>[C:12]([CH2:13][CH:14]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:15]1[CH:19]=[CH:18][S:17][CH:16]=1)#[N:29]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 8929Sodium CyanideHCID 59161758HCID 59161758, compound

Product 1

HCID 59161750HCID 59161750, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To 3-(tert-butoxycarbonylamino)-3-(thiophen-3-yl)propyl 4-methylbenzenesulfonate (E73B) in DMSO is added NaCN, and the solution is heated to 90° C. for 2 hours. The reaction is cooled, poured into NaCl (sat), and extracted with EtOAc. The organics are dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 25% EtOAc/Hexanes) gives pure tert-butyl 2-cyano-1-(thiophen-3-yl)ethylcarbamate (E73C).

Workup

  1. temperatureThe reaction is cooled
  2. extractionextracted with EtOAc
  3. dry with materialThe organics are dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-4b8a4fbd39194938811cc25cf8ab0238
Source dataset
uspto-grants-2014_06
Patent number
US08759388B2

Reaction notes

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