(2S,3S)-2-((4R)-2-benzhydryl-4-phenyl-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester → (2S,3S)-3-hydroxy-2-((1S)-2-hydroxy-1-phenyl-ethylamino)-4-methyl-pentanoic acid tert-butyl ester

HRID 25684Notes

Reaction equation

HRID 25684 reaction equation
[C:1]([O:5][C:6](=[O:37])[C@@H:7]([N:13]1[C@H:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][O:15]C1C(C1C=CC=CC=1)C1C=CC=CC=1)[C@@H:8]([OH:12])[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.O.C(O)=O>[C:1]([O:5][C:6](=[O:37])[C@@H:7]([NH:13][C@@H:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:16][OH:15])[C@@H:8]([OH:12])[CH:9]([CH3:11])[CH3:10])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 69752347(2S,3S)-2-((4R)-2-benzhydryl-4-phenyl-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester

Product 1

HCID 59065909(2S,3S)-3-hydroxy-2-((1S)-2-hydroxy-1-phenyl-ethylamino)-4-methyl-pentanoic acid tert-butyl esterYield 55%

Reagents, catalysts & solvents 1

HCID 86587932Formic acid tetrahydrofuran waterSolvent

Procedure

A solution of (2S,3S)-2-((4R)-2-benzhydryl-4-phenyl-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester (600 mg, 1.196 mmole, obtained from Reference Example 11) in a mixture of tetrahydrofuran : water: formic acid (3:1:1) was stirred at room temperature for 20 h. The volatile was removed in vacuo, and the residue was dissolved in aqueous sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate (3 times), and the extracts were combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (flash column, silica gel, methylene chloride:methanol:diethyl ether=90:2:10) to give (2S,3S)-3-hydroxy-2-((1S)-2-hydroxy-1-phenyl-ethylamino)-4-methyl-pentanoic acid tert-butyl ester as a white solid (211 mg, 55%).

Workup

  1. customThe volatile was removed in vacuo
  2. dissolutionthe residue was dissolved in aqueous sodium bicarbonate solution
  3. extractionThe aqueous layer was extracted with ethyl acetate (3 times)
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed (flash column, silica gel, methylene chloride:methanol:diethyl ether=90:2:10)

Sources & evidence

ORD record
ord-39ddf7946d6548939fc85c664ef99ef5
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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