Triethylsilane → (S)-4-Benzyl-3-((S)-3-{4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-2-ethoxy-propionyl)-oxazolidin-2-one

HRID 2215195Notes

Reaction equation

HRID 2215195 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:44])[C@@H:15]([O:41][CH2:42][CH3:43])[C@@H:16]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([O:28][CH2:29][CH2:30][C:31]2[N:32]=[C:33]([C:37]([CH3:40])([CH3:39])[CH3:38])[O:34][C:35]=2[CH3:36])=[CH:20][CH:19]=1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:44])[C@@H:15]([O:41][CH2:42][CH3:43])[CH2:16][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([O:28][CH2:29][CH2:30][C:31]2[N:32]=[C:33]([C:37]([CH3:40])([CH3:38])[CH3:39])[O:34][C:35]=2[CH3:36])=[CH:20][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 11563395(S)-4-Benzyl-3-((2S,3R)-3-{4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-2-ethoxy-3-hydroxy-propionyl)-oxazolidin-2-one

Product 1

HCID 11599585(S)-4-Benzyl-3-((S)-3-{4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-2-ethoxy-propionyl)-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.267 g of the above prepared (S)-4-benzyl-3-((2S,3R)-3-{4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-2-ethoxy-3-hydroxy-propionyl)-oxazolidin-2-one (0.444 mmol) was dissolved in 1.4 ml of trifluoroacetic acid, treated at 0° with 0.353 ml of triethylsilane (5 eq.) and then kept for 4 h at 0°, when TLC indicated the disappearance of starting material. The reaction mixture was then poured onto crashed ice/AcOEt/NaHCO3, the organic layer washed with water (pH of aq. phase˜8), dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=65/35) delivered 0.237 g of the title compound as white foam.

Workup

  1. additionThe reaction mixture was then poured
  2. washthe organic layer washed with water (pH of aq. phase˜8)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-7ba4824f1da34e2d968918c67519d720
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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