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

HRID 20058Notes

Reaction equation

HRID 20058 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-0737efb85022439ba9ec17ec97424d0a
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Reaction notes

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