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

HRID 1371242Notes

Reaction equation

HRID 1371242 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(N(CC)CC)C.C(O)C.[H][H]>[Pd].ClCCl.CO.C(N(CC)CC)C>[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

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 16086982(2R)-5-(Benzyloxycarbonylamino)-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-olHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21913430dichloromethane MeOH Et3NSolvent

Procedure

In a three neck-flask, 150 mg of 20% palladium/carbon were added to the solution of (2R)-5-(Benzyloxycarbonylamino)-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol (3.0 g, i.e. 5.27 mmol) and 6 ml of triethylamine in 300 ml of HPLC-grade ethanol, Air was discharged under vacuum then the flask was loaded with hydrogen. The reaction mixture was stirred at room temperature for 2 hours then the catalyst was filtered off by membrane filtration and the filtrate was concentrated to provide a homogenous white solid as shown by TLC, to be used as such in the next step with no further purifcation, Rf=0.2, dichlormethane-methanol-triethylamine 5:10.5, m.p.=47–48° C.

Workup

  1. filtrationthe catalyst was filtered off by membrane filtration
  2. concentrationthe filtrate was concentrated
  3. customto provide a homogenous white solid

Sources & evidence

ORD record
ord-08aebf35484b49d7bc986b8bc40e7733
Source dataset
uspto-grants-2007_01
Patent number
US07157092B1

Reaction notes

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