Potassium ethanethioate → HCID 131735876, compound

HRID 2207109Notes

Reaction equation

HRID 2207109 reaction equation
CS(O[CH:6]([C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=1)[C@@H:7]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:8])(=O)=O.[C:31](=[S:34])([O-:33])[CH3:32].[K+]>CN(C=O)C.CCOC(C)=O.CCCCCC>[C:31](=[O:33])([S:34][CH:6]([C:17]1[CH:22]=[C:21]([C:23]([F:24])([F:26])[F:25])[CH:20]=[C:19]([C:27]([F:29])([F:28])[F:30])[CH:18]=1)[C@@H:7]([NH:9][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH3:8])[CH3:32]

Participants

6

Reactant 2

HCID 23670855Potassium ethanethioateHCID 90238121HCID 90238121, compound

Product 1

HCID 131735876HCID 131735876, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S)-1-(3,5-bis(trifluoromethyl)phenyl)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate (1.0 g, 2.15 mmol) and potassium ethanethioate (0.736 g, 6.45 mmol) were combined in DMF (5 ml). The reaction was stirred at room temperature for 5 hours under a N2 atmosphere. The reaction was diluted with 30% EtOAc in hexane, washed with water, then brine, dried over Na2SO4, filtered and concentrated. The compound was purified by column chromatography to yield S-((2S)-1-(3,5-bis(trifluoromethyl)phenyl)-2-((tert-butoxycarbonyl)amino)propyl) ethanethioate. 1H NMR (500 MHz, CDCl3): δ 7.84 (s, 2H); 7.79 (s, 1H); 4.91 (s, 1H); 4.51 (s, 1H); 4.21 (s, 1H); 2.40 (s, 3H); 1.38 (s, 9H); 1.19 (d, J=6.9 Hz, 3H).

Workup

  1. washwashed with water
  2. dry with materialbrine, dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe compound was purified by column chromatography

Sources & evidence

ORD record
ord-f8d3b17432a8421ead16ff86d8444227
Source dataset
uspto-grants-2016_06
Patent number
US09376408B2

Reaction notes

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