HCID 69101439, compound → HCID 69101334, compound

HRID 394013Notes

Reaction equation

HRID 394013 reaction equation
C(OC([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][C@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:19]1)=[O:15])=O)C1C=CC=CC=1.[H][H]>CO.Cl.CO.[OH-].[Pd+2].[OH-].[C]>[NH2:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][C@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[CH2:19]1)=[O:15]

Participants

6

Reactant 2

HCID 69101439HCID 69101439, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69101334HCID 69101334, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

To a solution of 770 mg of 3-(benzyloxycarbonyl)amino-N-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}propanamide in 12 ml of methanol, 0.5 ml of 10% hydrochloric acid-methanol and 15 mg of 20% palladium hydroxide-carbon catalyst were added, followed by 44 hours' stirring under 3 atmospheres of hydrogen. Filtering the catalyst off, the solvent was distilled off under reduced pressure, and the residue was rendered weakly basic with saturated aqueous sodium bicarbonate solution. The product was extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by means of silica gel column chromatography (eluting solvent: chloroform-chloroform/methanol/28% aqueous ammonia=100/10/1) to provide 391 mg of the title compound.

Workup

  1. filtrationFiltering the catalyst off, the solvent
  2. distillationwas distilled off under reduced pressure
  3. extractionThe product was extracted with chloroform
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by means of silica gel column chromatography (eluting solvent: chloroform-chloroform/methanol/28% aqueous ammonia=100/10/1)

Sources & evidence

ORD record
ord-e8eab018961144b0ae0cc62dc83e0723
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

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