HCID 54302115, compound → HCID 9872611, compound

HRID 259909Notes

Reaction equation

HRID 259909 reaction equation
[CH2:1]([N:8]([C@H:16]([C:24](=[O:42])[CH:25]=[C:26]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CC(C)=O>[CH2:1]([N:8]([C@H:16]([C:24](=[O:42])[CH2:25][C@@H:26]([NH:34][C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 54302115HCID 54302115, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9872611HCID 9872611, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

An autoclave was charged with (2S)-2-(N,N-dibenzylamino)-5-tert-butoxycarbonylamino-1,6-diphenyl-4-hexen-3-one (0.56 g, 1 mmol), 25 mg of 3%-Pd-alumina and 5 ml of acetone. After introducing hydrogen under a pressure of 10 atm, the contents were stirred at 50° C. for 9 hours. The reaction mixture was filtered through a celite pad to remove the catalyst, and the filtrate was concentrated under reduced pressure to obtain 0.47 g (yield: 83%) of the title compound. 1H-NMR indicated that the purity of the (2S,5S) isomer was 95% or higher.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-907a621af1a744008c0fd2192143b658
Source dataset
uspto-grants-1996_06
Patent number
US05523458

Reaction notes

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