Ethanol → HCID 86585854, compound

HRID 1783223Notes

Reaction equation

HRID 1783223 reaction equation
[O:1]1[CH2:3][C@@H:2]1[C@@H:4]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C@@H:23]1([NH2:33])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)CCC1.[CH2:34]([OH:36])C>>[CH2:5]([C@H:4]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:2]([OH:1])[CH2:3][NH:33][CH2:23][C:32]1[CH:31]=[CH:30][CH:29]=[C:28]([O:36][CH3:34])[CH:27]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 70580741-Aminotetralin, (S)-HCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Product 1

HCID 86585854HCID 86585854, compound

Procedure

A mixture of benzyl (1S)-1-[(2S)-oxiranyl]-2-phenylethylcarbamate (V, 0.22 g, 0.74 mmol), 3-methoxybenzylamine (VI, 0.13 g, 0.92 mmol), and ethanol (2 mL) is stirred at reflux for 2.3 hours and then cooled and concentrated under reduced pressure. The residue is chouromatographed (silica gel; methanol/dichloromethane/ammonium hydroxide, 4/96/trace) to give the title compound, MS m/z at (m+H)+=435.2.

Workup

  1. temperatureat reflux for 2.3 hours
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-248a10502437472580dade79efab34be
Source dataset
uspto-grants-2009_03
Patent number
US07498436B2

Reaction notes

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