Triethylsilane → (4S)-3-[(2S)-3-(4-ethoxyphenyl)-2-isopropoxypropanoyl]-4-benzyl-1,3-oxazolan-2-one

HRID 1985432Notes

Reaction equation

HRID 1985432 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10](O)[C@H:11]([O:27][CH:28]([CH3:30])[CH3:29])[C:12]([N:14]2[C@@H:18]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:17][O:16][C:15]2=[O:26])=[O:13])=[CH:6][CH:5]=1)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C@H:11]([O:27][CH:28]([CH3:29])[CH3:30])[C:12]([N:14]2[C@@H:18]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:17][O:16][C:15]2=[O:26])=[O:13])=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 57719757(4S)-3-[(3R,2S)-3-(4-ethoxyphenyl)-3-hydroxy-2-isopropoxypropanoyl]-4-benzyl-1,3-oxazolan-2-one

Product 1

HCID 57719764(4S)-3-[(2S)-3-(4-ethoxyphenyl)-2-isopropoxypropanoyl]-4-benzyl-1,3-oxazolan-2-oneYield 101%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7.2 g of (4S)-3-[(3R,2S)-3-(4-Ethoxyphenyl)-3-hydroxy-2-isopropoxypropanoyl]-4-benzyl-1,3-oxazolan-2-one was dissolved in 200 ml of trifluoroacetic acid, 40 ml of triethylsilane was added, and the mixture was stirred for 24 hours. The solvent was evaporated, and the residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate), to give 7.0 g of (4S)-3-[(2S)-3-(4-ethoxyphenyl)-2-isopropoxypropanoyl]-4-benzyl-1,3-oxazolan-2-one as a colorless solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0aa4f5492f3d48e0af0bbf303dc39854
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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