Triethylsilane → (S)-4-Benzyl-3-((2S)-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionyl)-oxazolidin-2-one

HRID 479123Notes

Reaction equation

HRID 479123 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:42][CH3:43])[C@H:16](O)[C:17]1[C:22]2[S:23][CH:24]=[CH:25][C:21]=2[C:20]([O:26][CH2:27][CH2:28][C:29]2[N:30]=[C:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:32][C:33]=2[CH3:34])=[CH:19][CH:18]=1)[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:42][CH3:43])[CH2:16][C:17]1[C:22]2[S:23][CH:24]=[CH:25][C:21]=2[C:20]([O:26][CH2:27][CH2:28][C:29]2[N:30]=[C:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:32][C:33]=2[CH3:34])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 11387920(S)-4-Benzyl-3-((2S,3R)-3-hydroxy-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionyl)-oxazolidin-2-one

Product 1

HCID 11444748(S)-4-Benzyl-3-((2S)-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionyl)-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The above prepared (S)-4-benzyl-3-((2S,3R)-3-hydroxy-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionyl)-oxazolidin-2-one (0.255 g, 0.42 mmol) was dissolved in 2.2 ml of trifluoroacetic acid, treated at 0° with 0.663 ml of triethylsilane (10 eq.) and then kept for 3 h at ambient temperature, when TLC indicated the disappearance of starting material. The reaction mixture was poured onto crashed ice/AcOEt/NaHCO3, the organic layer washed with water and brine (pH of aq. phase˜8), dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=7/3) delivered 0.196 g of the title compound as colorless foam.

Workup

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

Sources & evidence

ORD record
ord-d3e858c3db854e1bab471d962413da41
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

Loading…