Triethylsilane → (S)-4-Benzyl-3-(3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(2S)-methoxy-propionyl)-oxazolidin-2-one

HRID 1394749Notes

Reaction equation

HRID 1394749 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:51])[C@@H:15]([O:49][CH3:50])[C@@H:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][C:27]2[N:28]=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:30][C:31]=2[CH3:32])=[CH:20][C:19]=1[O:39][Si:40]([CH3:48])([CH3:47])[C:41]([CH3:46])([CH3:45])[CH:42]([CH3:44])[CH3:43])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:51])[C@@H:15]([O:49][CH3:50])[CH2:16][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][C:27]2[N:28]=[C:29]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[O:30][C:31]=2[CH3:32])=[CH:20][C:19]=1[O:39][Si:40]([CH3:47])([CH3:48])[C:41]([CH3:45])([CH3:46])[CH:42]([CH3:43])[CH3:44])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69280419(S)-4-Benzyl-3-((2S,3R)-3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-3-hydroxy-2-methoxy-propionyl)-oxazolidin-2-one

Product 1

HCID 69283498(S)-4-Benzyl-3-(3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(2S)-methoxy-propionyl)-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The above prepared (S)-4-benzyl-3-((2S,3R)-3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-3-hydroxy-2-methoxy-propionyl)-oxazolidin-2-one (2.8 g, 3.91 mmol) was dissolved in 10 ml of trifluoroacetic acid, treated at 0° C. with 10 ml of triethylsilane and then kept for 3 hours at ambient temperature. The reaction mixture was then poured onto crashed ice/AcOEt/NaOH (1M), the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated to dryness. Flash chromatography (SiO2, heptane/AcOEt) delivered 1.6 g (58%) of the title compound (purity ˜80%) as a yellow foam.

Workup

  1. additionThe reaction mixture was then poured
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-6bb9377841a14fbfb30269b29c283ebe
Source dataset
uspto-grants-2008_03
Patent number
US07348349B2

Reaction notes

Loading…