(2R)-5-(Benzyloxycarbonylamino)-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol → (2R)-5-amino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol

HRID 1920601

Reaction equation

HRID 1920601 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([NH:18][C:19](=[O:41])[CH2:20][C@H:21]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:16][OH:17])=O)C1C=CC=CC=1.C(O)C.CCO.[H][H]>C(N(CC)CC)C.CCN(CC)CC.[Pd]>[NH2:11][CH2:12][CH2:13][CH2:14][C@@H:15]([NH:18][C:19](=[O:41])[CH2:20][C@H:21]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:16][OH:17]

Participants

6

Reactant 3

HCID 16086982(2R)-5-(Benzyloxycarbonylamino)-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-olHCID 57419690EtOH EthanolHCID 178418361HCID 178418361, compound

Product 1

HCID 11476040(2R)-5-amino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22592508triethylamine TriethylamineSolvent

Procedure

In a three-neck flask, the catalyst (150 mg of 20% palladium/carbon) was added to the solution of (2R)-5-(benzyloxycarbonylamino)-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol (3.0 g; 5.27 mmol) in a mixture of triethylamine Et3N (6 ml)/HPLC-grade ethanol EtOH (300 ml). Air was discharged under vacuum then the flask was loaded with hydrogen. The reaction mixture was hydrogenated at room temperature for 2 hours then the catalyst was filtered off and the filtrate was concentrated to provide the desired product as a homogenous white solid. Rf=0.2, 5/1 0/0.5 CH2Cl2-MeOH-Et3N, m.p.=47-48° C.

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2bc368e9abfa493bb09096be0109c576
Source dataset
uspto-grants-2012_05
Patent number
US08173133B2

Linked notes

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