Dimethylformamide → HCID 88850772, compound

HRID 1405948Notes

Reaction equation

HRID 1405948 reaction equation
[H-].[Na+].CN(C)C=O.[SH:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].CC1C=CC(S(O[CH2:30][C:31]([F:34])([F:33])[F:32])(=O)=O)=CC=1>O>[F:32][C:31]([F:34])([F:33])[CH2:30][S:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiol

Product 1

HCID 88850772HCID 88850772, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.7 g of sodium hydride was added to 30 ml of dry dimethylformamide, and then 7.5 g of tert-butyl 2-mercaptoethylaminoformate. Upon the end of the addition, the mixture was stirred for 1 h, and then slowly added with 2,2,2-trifluoroethyl (4-methylphenyl)sulfonate. Upon the end of the addition, the mixture was warmed to room temperature, and stirred overnight. The mixture was poured to water, extracted with diethyl ether, washed with 0.5M sodium hydroxide aqueous solution and then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, distilled to remove the solvent, and subjected to a column chromatography to obtain 5.4 g of light yellow oily liquid, yield 53.8%.

Workup

  1. additionUpon the end of the addition
  2. additionUpon the end of the addition
  3. stirringstirred overnight
  4. extractionextracted with diethyl ether
  5. washwashed with 0.5M sodium hydroxide aqueous solution
  6. dry with materialwith saturated sodium chloride solution, dried over anhydrous sodium sulfate
  7. distillationdistilled
  8. customto remove the solvent

Sources & evidence

ORD record
ord-5b412be920a146f1ab74f23b2e8c6d20
Source dataset
uspto-grants-2014_12
Patent number
US08916574B2

Reaction notes

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