Tetrabutylammonium Fluoride Trihydrate → HCID 69124594, compound

HRID 2252427Notes

Reaction equation

HRID 2252427 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[C@@H:12]([NH:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C@@H:13]([CH2:29][CH2:30][C@H:31]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[C:14](N1[C@@H](CC2C=CC=CC=2)COC1=O)=[O:15])[CH:2]=[CH2:3].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OC)(C)(C)C>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[C@H:12]1[N:47]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:14](=[O:15])[C@@H:13]1[CH2:29][CH2:30][C@H:31]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[C:32]1[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 69117821HCID 69117821, compound

Product 1

HCID 69124594HCID 69124594, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

(4S)-3-[(2R,5S)-2-[(S)-[2-(Allyloxy)-4-bromophenyl](anilino)methyl]-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one (1.2 g, 1.5 mmol) was dissolved in anhydrous methyl tert-butyl ether (10 mL) and stirred at room temperature under nitrogen. N,O-bistrimethylsilylacetamide (1.1 mL, 4.5 mmol) was added followed by a catalytic amount (˜5 mg) of tetrabutylammonium fluoride trihydrate. The reaction was stirred at room temperature for 19 h, quenched at room temperature with glacial acetic acid (160 μL) and partitioned between ethyl acetate and water and separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with a saturated sodium bicarbonate solution, water, brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography (120 g silica gel, 1% to 85% ethyl acetate-hexane) to afford (3R,4S)-4-[2-(allyloxy)-4-bromophenyl]-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-2-one (816 mg, 87% yield); Rf 0.56 (1:4 ethyl acetate-hexane).

Workup

  1. stirringThe reaction was stirred at room temperature for 19 h
  2. customquenched at room temperature with glacial acetic acid (160 μL)
  3. custompartitioned between ethyl acetate and water
  4. customseparated
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layers were washed with a saturated sodium bicarbonate solution, water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography (120 g silica gel, 1% to 85% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-31bcb2d004c14fa398408b2368884117
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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