(2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methyl-cyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester → (2R,5R)-5-[(1S,2S)-2-Acetylamino-1-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester

HRID 20428Notes

Reaction equation

HRID 20428 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:35])[C@@H:15]([NH:31][C:32](=[O:34])[CH3:33])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23]CC3C=CC=CC=3)[CH:18]=2)[CH2:12][O:11][C@@H:10]([O:36][CH2:37][C:38]2([CH3:43])[CH2:42][CH2:41][CH2:40][CH2:39]2)[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:35])[C@@H:15]([NH:31][C:32](=[O:34])[CH3:33])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[CH2:12][O:11][C@@H:10]([O:36][CH2:37][C:38]2([CH3:43])[CH2:39][CH2:40][CH2:41][CH2:42]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 68561840(2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methyl-cyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 68562669(2R,5R)-5-[(1S,2S)-2-Acetylamino-1-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl esterYield 98.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Hydrogenate (2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester (244 mg) in methanol (15 mL) with 20% palladium hydroxide on carbon (26 mg) at 50 psi hydrogen for 18 hours. Filter and concentrate to give the desired compound (204 mg). MS(ES): m/z=507 [M+H]

Workup

  1. filtrationFilter
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-3f30fb1c0fa74e61bd19f8a701e01af4
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

Loading…