5-(R)-[1-(S)-benzyloxy-2-(S)-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-(S)-(3-methylbutyl)-morpholine-4-carboxylic acid tert-butyl ester → HCID 68558729, compound

HRID 20356Notes

Reaction equation

HRID 20356 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([O:40]CC2C=CC=CC=2)[C@@H:15]([N:25](CC2C=CC=CC=2)CC2C=CC=CC=2)[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[CH2:12][O:11][C@@H:10]([CH2:48][CH2:49][CH:50]([CH3:52])[CH3:51])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:40])[C@@H:15]([NH2:25])[CH2:16][C:17]2[CH:18]=[C:19]([F:24])[CH:20]=[C:21]([F:23])[CH:22]=2)[CH2:12][O:11][C@@H:10]([CH2:48][CH2:49][CH:50]([CH3:52])[CH3:51])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 685638025-(R)-[1-(S)-benzyloxy-2-(S)-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-(S)-(3-methylbutyl)-morpholine-4-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound2×

Product 1

HCID 68558729HCID 68558729, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

Procedure

Dissolve 5-(R)-[1-(S)-benzyloxy-2-(S)-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-(S)-(3-methylbutyl)-morpholine-4-carboxylic acid tert-butyl ester (187.7 mg, 0.263 mmol) in methanol (10 mL). Add 20% palladium hydroxide on carbon 100 mg) and hydrogenate at one atmosphere hydrogen gas for 18 hours. Add more 20% palladium hydroxide on carbon (100 mg) and further hydrogenate at one atmosphere hydrogen gas for 5 hours. Filter and concentrate to give the desired compound (107.8 mg, 93%).

Workup

  1. filtrationFilter
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-d95a93a22df141bb8bf58a0f577d0c39
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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