Ethyl Acetate → N1-[(1S,2R)-3-amino-1-(3,5-difluorobenzyl)-2-hydroxypropyl]-5-methyl-N3,N3-dipropylisophthalamide Acetic Acid Salt

HRID 1783200

Reaction equation

HRID 1783200 reaction equation
[N:1]([CH2:4][C@@H:5]([OH:35])[C@@H:6]([NH:16][C:17](=[O:34])[C:18]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:20]([C:21]([N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])=[O:22])[CH:19]=1)[CH2:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[CH:9]=1)=[N+]=[N-].[C:36]([O:39]CC)(=[O:38])[CH3:37]>C(O)(=O)C.[Pd]>[C:36]([OH:39])(=[O:38])[CH3:37].[NH2:1][CH2:4][C@@H:5]([OH:35])[C@@H:6]([NH:16][C:17](=[O:34])[C:18]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:20]([C:21]([N:23]([CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28][CH3:29])=[O:22])[CH:19]=1)[CH2:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[CH:9]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 86585849N1-[(1S,2R)-3-azido-1-(3,5-difluorobenzyl)-2-hydroxypropyl]5-methyl-N3,N3-dipropylisophthalamide

Product 1

HCID 68609581N1-[(1S,2R)-3-amino-1-(3,5-difluorobenzyl)-2-hydroxypropyl]-5-methyl-N3,N3-dipropylisophthalamide Acetic Acid Salt

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

N1-[(1S,2R)-3-azido-1-(3,5-difluorobenzyl)-2-hydroxypropyl]5-methyl -N3,N3-dipropylisophthalamide (XV, EXAMPLE 167, 0.3 9, 0.62 mmole) in ethyl acetate (20 ml) and acetic acid (5ml) is placed in a Parr pressure bottle. Palladium on carbon (10%, 5 g) is added and the mixture shaken under hydrogen at 50 psi for 2 hours. The mixture is filtered through a diatomaceous earth and the filtrate is concentrated to give the title compound; MS (MH+)=462.

Workup

  1. filtrationThe mixture is filtered through a diatomaceous earth
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-f1428e371c4e4b2ba18d67318db642aa
Source dataset
uspto-grants-2009_03
Patent number
US07498436B2

Linked notes

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