Triethylsilane → HCID 18653188, compound

HRID 1464824Notes

Reaction equation

HRID 1464824 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-03ca4eb839b74aff8c3cb561a876f10c
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

Loading…