[1-Benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl]-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester → (1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

HRID 1786648Notes

Reaction equation

HRID 1786648 reaction equation
C(OC(=O)[N:10]([CH2:15][CH:16]([OH:37])[CH:17]([NH:25][C:26]([O:28][CH:29]1[CH:36]2[CH:32]([O:33][CH2:34][CH2:35]2)[O:31][CH2:30]1)=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:11][CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1>C(O)C.[Pd]>[O:31]1[CH:32]2[O:33][CH2:34][CH2:35][CH:36]2[CH:29]([O:28][C:26](=[O:27])[NH:25][CH:17]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:16]([OH:37])[CH2:15][NH:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:30]1

Participants

4

Reactant 1

HCID 66769651[1-Benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl]-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester

Product 1

HCID 21055240(1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl esterYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of [3-(hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-isobutyl-carbamic acid benzyl ester 18 (5.5 g, 10.4 mmol) and 550 mg of 10% Pd/C in 130 ml of ethanol was stirred under a hydrogen atmosphere overnight. The catalyst was removed by filtration through Celite®, and the solution was evaporated to dryness to yield (1-benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 19 (4.0 g, 97%) as a white solid. TLC: Rf 0.36 (5:15:85 triethylamine:methanol:ethyl acetate). MS 393 (MH)+.

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. customthe solution was evaporated to dryness

Sources & evidence

ORD record
ord-da7c1d34ef7f4336bbb01a45cf299d6f
Source dataset
uspto-grants-2009_03
Patent number
US07507763B2

Reaction notes

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