Triethylsilane → (S)-4-Benzyl-3-[(S)-3-(4-hydroxyphenyl)-2-(4-methylphenoxy)propionyl]oxazolidin-2-one

HRID 1268948Notes

Reaction equation

HRID 1268948 reaction equation
C([SiH](CC)CC)C.[CH2:8]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:40])[C@@H:22]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)[C@H:23](O)[C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>FC(F)(F)C(O)=O>[CH2:8]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:40])[C@@H:22]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69504636(S)-4-Benzyl-3-[(2S,3R)-3-hydroxy-3-(4-hydroxyphenyl)-2-(4-methylphenoxy)propionyl]oxazolidin-2-one

Product 1

HCID 69504567(S)-4-Benzyl-3-[(S)-3-(4-hydroxyphenyl)-2-(4-methylphenoxy)propionyl]oxazolidin-2-oneYield 85.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (24.0 ml) was added at room temperature to a solution of (S)-4-benzyl-3-[(2S,3R)-3-hydroxy-3-(4-hydroxyphenyl)-2-(4-methylphenoxy)propionyl]oxazolidin-2-one (8.15 g) obtained from Reference example 20(c) in trifluoroacetic acid (90 ml), then the mixture was stirred for 18 hours and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution, a 1N aqueous solution of hydrochloric acid and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were filtered off and washed with a mixed solvent of isopropyl ether and hexane to give the target compound (6.70 g) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materiala 1N aqueous solution of hydrochloric acid and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe obtained crystals were filtered off
  7. washwashed with a mixed solvent of isopropyl ether and hexane

Sources & evidence

ORD record
ord-fa22073ed3724617974207b48c2255ca
Source dataset
uspto-grants-2007_04
Patent number
US07199139B2

Reaction notes

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