(2S,3S)-3-hydroxy-2-((1S)-2-hydroxy-1-phenyl-ethylamino)-4-methyl-pentanoic acid tert-butyl ester → (2S,3S)-2-amino-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester

HRID 25685Notes

Reaction equation

HRID 25685 reaction equation
[C:1]([O:5][C:6](=[O:23])[C@@H:7]([NH:13][C@@H](C1C=CC=CC=1)CO)[C@@H:8]([OH:12])[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6](=[O:23])[C@@H:7]([NH2:13])[C@@H:8]([OH:12])[CH:9]([CH3:10])[CH3:11])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 59065909(2S,3S)-3-hydroxy-2-((1S)-2-hydroxy-1-phenyl-ethylamino)-4-methyl-pentanoic acid tert-butyl ester

Product 1

HCID 15408106(2S,3S)-2-amino-3-hydroxy-4-methyl-pentanoic acid tert-butyl esterYield 87.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2S,3S)-3-Hydroxy-2-((1S)-2-hydroxy-1-phenyl-ethylamino)-4-methyl-pentanoic acid tert-butyl ester (450 mg, 1.39 mmole, obtained from Reference Example 12) was hydrogenated using 10% palladium on carbon (120 mg) in methanol (100 ml) under atmospheric pressure at room temperature. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The residue was chromatographed (flash column, silica gel, 20-30% methanol in diethyl ether) to give (2S,3S)-2-amino-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester as a white solid (246 mg, 87%).

Workup

  1. customat room temperature
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed (flash column, silica gel, 20-30% methanol in diethyl ether)

Sources & evidence

ORD record
ord-413b2844458642dcbbb0cbf379c4dec1
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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