(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane → Trifluoroacetic acid

HRID 1009166Notes

Reaction equation

HRID 1009166 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:16])([C:12]([F:15])([F:14])[F:13])[CH2:6][C@@H:5]2[NH2:17].[O:18]1[CH2:20][C@@H:19]1[C@@H:21]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:16])([C:12]([F:14])([F:13])[F:15])[CH2:6][C@@H:5]2[NH:17][CH2:20][C@@H:19]([OH:18])[C@@H:21]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:7]([OH:18])([C:12]([F:15])([F:14])[F:13])=[O:8]

Participants

5

Reactant 2

HCID 9903372(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutaneHCID 67305954(4S)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-amine

Product 2

HCID 6422Trifluoroacetic acidHCID 86614140HCID 86614140, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (4S)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-amine (179 mg, 577 μmol) and tert-butyl(S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (198 mg, 750 μmol) in ethanol was heated at reflux for 16 h. At this point, there was still the starting amine left. An additional 1.3 eq of epoxide was added to the reaction, and continued to reflux for 6 h. The resulted mixture was concentrated and purified on Shimadzu HPLC to afford the title compound as a TFA salt. MS m/z: 573, 575.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. waitleft
  4. temperatureto reflux for 6 h
  5. concentrationThe resulted mixture was concentrated
  6. custompurified on Shimadzu HPLC

Sources & evidence

ORD record
ord-680613adb247428da1f07631a33013c2
Source dataset
uspto-grants-2011_07
Patent number
US07973047B2

Reaction notes

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