Triethylsilane → HCID 69556698, compound

HRID 479135Notes

Reaction equation

HRID 479135 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:49])[C@@H:15]([O:47][CH3:48])[C@H:16](O)[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([O:27][CH2:28][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=3)[O:33][C:34]=2[CH3:35])=[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:49])[C@@H:15]([O:47][CH3:48])[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([O:27][CH2:28][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:37]=[CH:38][C:39]([C:42]([F:43])([F:44])[F:45])=[CH:40][CH:41]=3)[O:33][C:34]=2[CH3:35])=[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 69557082HCID 69557082, compound

Product 1

HCID 69556698HCID 69556698, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.837 g of the above prepared (S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-(4-{2-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-ethoxy}-naphthalen-1-yl)-propionyl]-oxazolidin-2-one (1.23 mmol) was dissolved in 3.2 ml of trifluoroacetic acid, treated at 0° with 0.977 ml of triethylsilane (5 eq.) and then kept for 16 h at ambient temperature, 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 and brine (pH of aq. phase˜8), dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=7/3) delivered 0.702 g of the title compound as white foam.

Workup

  1. additionThe reaction mixture was then 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-96586fee321e40fc91c4bf77da8a2fdc
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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