tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate → [1-(3,5-Difluoro-benzyl)-2-hydroxy-3-(1-isobutylcarbamoyl-ethylamino)-propyl]-carbamic Acid Tert-Butyl Ester

HRID 14069Notes

Reaction equation

HRID 14069 reaction equation
[CH2:1]([NH:5][C:6](=[O:10])[C@H:7]([CH3:9])[NH2:8])[CH:2]([CH3:4])[CH3:3].[F:11][C:12]1[CH:13]=[C:14]([CH2:19][C@H:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C@H:21]2[CH2:23][O:22]2)[CH:15]=[C:16]([F:18])[CH:17]=1>C(O)(C)C>[C:27]([O:26][C:25](=[O:31])[NH:24][CH:20]([CH2:19][C:14]1[CH:13]=[C:12]([F:11])[CH:17]=[C:16]([F:18])[CH:15]=1)[CH:21]([OH:22])[CH2:23][NH:8][CH:7]([C:6](=[O:10])[NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])[CH3:9])([CH3:28])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamateHCID 13750006N1-Isobutyl-L-alaninamide

Product 1

HCID 21087184[1-(3,5-Difluoro-benzyl)-2-hydroxy-3-(1-isobutylcarbamoyl-ethylamino)-propyl]-carbamic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N1-Isobutyl-L-alaninamide (3.8 g, 26 mmol) and tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiran-2-yl]ethylcarbamate prepared by the method in Example S-3 (3.1 g, 10.4 mmol) in isopropanol (50 mL) are refluxed 4 h. The reaction is cooled and concentrated under reduced pressure. Purification by flash column chromatography (silica, 8% methanol/chloroform) gives the title compound. ESI MS m/z 444.1 [M+H]+.

Workup

  1. temperatureare refluxed 4 h
  2. temperatureThe reaction is cooled
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash column chromatography (silica, 8% methanol/chloroform)

Sources & evidence

ORD record
ord-1be4056efffd4947ba0508ca8c0247fe
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

Loading…