Triethylsilane → HCID 69877036, compound

HRID 1860041Notes

Reaction equation

HRID 1860041 reaction equation
C([SiH](CC)CC)C.[CH2:8]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:42])[C@@H:22]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]([CH3:41])[CH3:40])=[CH:35][CH:34]=1)[C@H:23](O)[C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>FC(F)(F)C(O)=O>[CH2:8]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:42])[C@@H:22]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]([CH3:40])[CH3:41])=[CH:35][CH:34]=1)[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69876585HCID 69876585, compound

Product 1

HCID 69877036HCID 69877036, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (30.2 ml) was added to a solution of (S)-4-benzyl-3-[(2S,3R)-3-hydroxy-3-(4-hydroxyphenyl)-2-(4-isopropylphenoxy)propionyl]oxazolidine-2-one (18.0 g), which is the product of Reference example 29(c), in trifluoroacetic acid (150 ml) at ambient temperature. The mixture was stirred for 18 hours. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was washed with saturated aqueous sodium hydrogencarbonate solution, aqueous hydrogen chloride solution (1N) and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=3/1 as the eluant to afford the desired compound (10.7 g) as colorless crystals.

Workup

  1. customat ambient temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. customthe layers were separated
  5. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogencarbonate solution, aqueous hydrogen chloride solution (1N) and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-df9a29b981c54a76ba00107ded530bb9
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

Loading…