tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate → HCID 58802705, compound

HRID 348875

Reaction equation

HRID 348875 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]2[CH2:13][O:12]2)[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.[CH:23]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][NH2:30])([CH3:25])[CH3:24]>C(O)(C)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]([OH:12])[CH2:13][NH:30][CH2:29][C:28]1[CH:31]=[CH:32][CH:33]=[C:26]([CH:23]([CH3:25])[CH3:24])[CH:27]=1

Participants

4

Reactant 2

HCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamateHCID 210858343-Isopropylbenzylamine Hydrochloride

Product 1

HCID 58802705HCID 58802705, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

tert-Butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiran-2-yl]ethylcarbamate (2.0 g, 6.7 mmol) and 3-isopropylbenzylamine hydrochloride (2.5 g, 13.5 mmol) in isopropanol (60 mL) are refluxed 3 h. The reaction is cooled and stirred 16 h. The solution is concentrated under reduced pressure, redissolved in chloroform, washed with 1N hydrochloric acid, saturated sodium bicarbonate, brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. Purification by flash chromatography (silica, 7% methanol/chloroform) gives the title compound in pure form. ESI MS m/z 449.3 [M+H]+.

Workup

  1. temperatureThe reaction is cooled
  2. concentrationThe solution is concentrated under reduced pressure
  3. dissolutionredissolved in chloroform
  4. washwashed with 1N hydrochloric acid, saturated sodium bicarbonate, brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography (silica, 7% methanol/chloroform)

Sources & evidence

ORD record
ord-60d492a4420849738eea277bf6ad3591
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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