HCID 14261125, compound → HCID 11151551, compound

HRID 1085668Notes

Reaction equation

HRID 1085668 reaction equation
[CH2:1]([NH:5][C:6](=[O:25])[C@H:7]([CH:22]([CH3:24])[CH3:23])[CH2:8][C@H:9]([OH:21])[C@@H:10]([N:18]=[N+]=[N-])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[CH2:1]([NH:5][C:6](=[O:25])[C@H:7]([CH:22]([CH3:24])[CH3:23])[CH2:8][C@H:9]([OH:21])[C@@H:10]([NH2:18])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 14261125HCID 14261125, compound

Product 1

HCID 11151551HCID 11151551, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

21.3 g (0.06 mol) of 5(S)-azido-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoic acid n-butylamide in 240 ml of methanol are hydrogenated for 2 hours in the presence of 5 g of 10% palladium-on-carbon. The reaction mixture is filtered, concentrated in a rotary evaporator, and the residue is recrystallised from hexane: m.p. 88.5°-90°; [α]D -27.2°±0.9° (c=1.1, CHCl3).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated in a rotary evaporator
  3. customthe residue is recrystallised from hexane

Sources & evidence

ORD record
ord-f3ab48c6f0264b6c8390bcd948da3862
Source dataset
uspto-grants-1991_04
Patent number
US05010189

Reaction notes

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