Ethanol → HCID 86585854, compound

HRID 1350963Notes

Reaction equation

HRID 1350963 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-0d07b7870207494c8af123d2eb02b577
Source dataset
uspto-grants-2007_05
Patent number
US07214715B2

Reaction notes

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