Hexane → HCID 136156243, compound

HRID 1032892Notes

Reaction equation

HRID 1032892 reaction equation
[CH:1]1([NH:7][C:8](=[O:24])[C@H:9]([CH:21]([CH3:23])[CH3:22])[NH:10][C:11](OCC2C=CC=CC=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:25]1([C:31]2[CH:38]=[CH:37][CH:36]=[C:33](C=O)[C:32]=2[OH:39])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCCCCC.C(OCC)(=O)C>CO.[C].[Pd]>[CH:1]1([NH:7][C:8](=[O:24])[C@H:9]([CH:21]([CH3:22])[CH3:23])[N:10]=[CH:11][C:33]2[C:32](=[C:31]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:38]=[CH:37][CH:36]=2)[OH:39])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 826228(S)-Benzyl (1-(cyclohexylamino)-3-methyl-1-oxobutan-2-yl)carbamateHCID 107031002-Formyl-6-phenylphenol

Product 1

HCID 136156243HCID 136156243, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 887MethanolSolvent

Procedure

The carbobenzoxy-(S)-valine cyclohexylamide (0.33 g, 1 mmol) was dissolved in methanol (30 ml) and the solution was stirred at room temperature for 3 hours in the presence of 5% palladium-carbon (30 mg) under a hydrogen gas atmosphere. After the reaction was over, the palladium-carbon catalyst was filtered off to obtain a colorless solution. To this solution was added 3-phenylsalicylaldehyde (0.22 g, 1.1 mmol). This solution was stirred at room temperature for 24 hours and concentrated under reduced pressure to obtain yellow solids. These solids were subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to obtain 0.29 g (76%) of the desired N-(3-phenylsalicylidene)-(S)-valine cyclohexylamide which was further recrystallized from ether. m.p. 87.0°-89.5° C. [α]26D +158.3° (c 1.02, CHCl3)

Workup

  1. filtrationwas filtered off
  2. customto obtain a colorless solution
  3. concentrationconcentrated under reduced pressure
  4. customto obtain yellow solids

Sources & evidence

ORD record
ord-1d490d2fca0d4039ad4851e2102700db
Source dataset
uspto-grants-1994_05
Patent number
US05308820

Reaction notes

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