Ethyl Acetate → HCID 59643959, compound

HRID 2252440Notes

Reaction equation

HRID 2252440 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([C@H:21]3[N:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:23](=[O:31])[C@@H:22]3[CH2:32][CH2:33][C@H:34]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)(C(C)(C)C)(C)C.[F-].[K+].C(OCC)(=O)C>CO>[Si:43]([O:42][C@H:34]([C:35]1[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=1)[CH2:33][CH2:32][C@@H:22]1[C@@H:21]([C:18]2[CH:19]=[CH:20][C:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=3)=[CH:16][CH:17]=2)[N:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:23]1=[O:31])([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 522689Potassium FluorideHCID 69116717HCID 69116717, compound

Product 1

HCID 59643959HCID 59643959, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3R,4S)-4-(3′-{[tert-Butyl(dimethyl)silyl]oxy}biphenyl-4-yl)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-2-one (0.60 g, 0.86 mmol) was stirred at room temperature in dry methanol (20 mL) under a nitrogen atmosphere. Potassium fluoride (0.10 g, 1.72 mmol) was added and the reaction mixture was stirred 1.5 h at room temperature. The solution was poured into ethyl acetate and washed successively with water (2×), 10% aqueous sodium bicarbonate, water and brine. The organic solution was dried over sodium sulfate, filtered, concentrated and purified by chromatography over silica gel using ethyl acetate-hexane (gradient: 5% ethyl acetate to 50%) to afford (3R,4S)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-(3′-hydroxybiphenyl-4-yl)-1-phenylazetidin-2-one (0.46 g, 92%) as a white foam; 1H NMR (300 MHz, CDCl3) δ 7.57 (d, J=8.2, Hz, 2H,) 7.37 (d, J=8.2 Hz, 2H), 6.9-7.4 (m, 12H), 6.8 (m, 1H), 4.9 (br s, 1H), 4.67 (t, J=6.0 Hz, 1H), 4.63 (d, J=2.5 Hz, 1H), 3.0-3.1 (m, 1H), 1.8-2.0 (m, 4H), 0.87 (s, 9H), 0.02 (s, 3H), −0.16 (s, 3H).

Workup

  1. washwashed successively with water (2×), 10% aqueous sodium bicarbonate, water and brine
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by chromatography over silica gel

Sources & evidence

ORD record
ord-4aa3cf9e3539418eb99f63f62a88ea54
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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