HCID 59494498, compound → HCID 59494704, compound

HRID 872017Notes

Reaction equation

HRID 872017 reaction equation
C([O:8][CH2:9][C@H:10]1[O:15][C@@H:14]([C:16]([N:18]([CH:34]2[CH2:36][CH2:35]2)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:21]=2)=[O:17])[CH2:13][N:12]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:11]1)C1C=CC=CC=1.[H][H]>CO.[OH-].[Pd+2].[OH-].[C]>[CH:34]1([N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:21]=2)[C:16]([C@@H:14]2[O:15][C@H:10]([CH2:9][OH:8])[CH2:11][N:12]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:13]2)=[O:17])[CH2:36][CH2:35]1

Participants

5

Reactant 2

HCID 59494498HCID 59494498, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59494704HCID 59494704, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

20% Palladium hydroxide-carbon (dry) (22 mg) was added to a solution of tert-butyl(2S,6R)-2-[(benzyloxy)methyl]-6-({cyclopropyl[4-methoxy-3-(3-methoxypropoxy)benzyl]amino}carbonyl)morpholin-4-carboxylate (220 mg) in methanol and the mixture was stirred under normal pressure of hydrogen atmosphere at room temperature for 6 hours. After filtration of insoluble materials through Celite, the filtrate was concentrated to give tert-butyl(2R,6S)-2-({cyclopropyl[4-methoxy-3-(3-methoxypropoxy)benzyl]amino}carbonyl)-6-(hydroxymethyl)morpholin-4-carboxylate (200 mg) as a pale yellow oil.

Workup

  1. filtrationAfter filtration of insoluble materials through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-73da1c27b23a46d09961d9f8363359e8
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

Loading…