Triethylsilane → HCID 18653188, compound

HRID 2253973Notes

Reaction equation

HRID 2253973 reaction equation
O[C@H:2]([C:22]1[CH:23]=[CH:24][C:25]2[O:30][C@H:29]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=4)=[CH:34][CH:33]=3)[CH:28]=[CH:27][C:26]=2[CH:47]=1)[C@H:3]([O:19][CH2:20][CH3:21])[C:4]([N:6]1[C@@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][O:8][C:7]1=[O:18])=[O:5].C([SiH](CC)CC)C>FC(F)(F)C(O)=O.CCOCC>[CH2:20]([O:19][C@H:3]([C:4]([N:6]1[C@@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][O:8][C:7]1=[O:18])=[O:5])[CH2:2][C:22]1[CH:23]=[CH:24][C:25]2[O:30][C@H:29]([CH2:31][C:32]3[CH:33]=[CH:34][C:35]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=4)=[CH:36][CH:37]=3)[CH:28]=[CH:27][C:26]=2[CH:47]=1)[CH3:21]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 54530437HCID 54530437, compound

Product 1

HCID 18653188HCID 18653188, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-6-{(1R,2S)-1-Hydroxy-2-ethoxy-3-[(S)-4-benzyl-2-oxo-3-oxazolidinyl]-3-oxopropyl}-2-[4-(3-fluorobenzyloxy)benzyl]-2H-benzopyran (80 mg, 0.13 mmol) was dissolved in trifluoroacetic acid (2 ml) and triethylsilane (0.20 ml) was added. After 30 minutes the solution was diluted with ether, washed with water (2×) and saturated sodium bicarbonate (2×), dried over magnesium sulfate and concentrated. The product was purified by flash-chromatography (hexanes/ethyl acetate, 2:1) and obtained as an oil (39 mg).

Workup

  1. washwashed with water (2×) and saturated sodium bicarbonate (2×)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe product was purified by flash-chromatography (hexanes/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-83b6258f873a414386ebe95b05578c84
Source dataset
uspto-grants-1993_08
Patent number
US05232945

Reaction notes

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