HCID 68561096, compound → HCID 68563661, compound

HRID 20343Notes

Reaction equation

HRID 20343 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][O:49][C:50](=[O:54])[CH2:51][CH2:52][CH3:53])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[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:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[CH2:12][O:11][C@@H:10]([CH2:48][O:49][C:50](=[O:54])[CH2:51][CH2:52][CH3:53])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 68561096HCID 68561096, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68563661HCID 68563661, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Dissolve (2R,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-butyryloxymethyl-morpholine-4-carboxylic acid tert-butyl ester (295 mg, 0.397 mmol) in ethanol (29 mL). Add 20% palladium hydroxide on carbon (330 mg) and stir under 1 atmosphere of hydrogen gas for 48 hours. Filter through a filtering agent and wash with ethanol. Concentrate the filtrate to give the desired compound as a white foam (188 mg, 100%).

Workup

  1. filtrationFilter through a filtering agent
  2. washwash with ethanol
  3. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-e09ff7f8a5644452bfc3792fcaa0c5db
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

Loading…