Hydrofluoric Acid → HCID 69257389, compound

HRID 2252439Notes

Reaction equation

HRID 2252439 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[C@@H:12]1[C@@H:15]([CH2:16][CH2:17][C@H:18]([O:26][Si](C(C)(C)C)(C)C)[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:14](=[O:34])[N:13]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:3])[CH3:2].F.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C>[C:1]([O:4][C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[C@@H:12]1[C@@H:15]([CH2:16][CH2:17][C@@H:18]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[OH:26])[C:14](=[O:34])[N:13]1[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 14917Hydrofluoric AcidHCID 62657Potassium Phosphate, TribasicHCID 59643928HCID 59643928, compoundHCID 178435178HCID 178435178, compound

Product 1

HCID 69257389HCID 69257389, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Bromo-2-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}phenyl acetate (140.0 mg, 0.223 mmol) was dissolved in acetonitrile (8.0 mL) and 48% hydrofluoric acid (0.8 mL) into a polypropylene Falcon® tube. The reaction was stirred for 4 h at room temperature and then poured into 0.5 M potassium phosphate (50 mL), extracted with 1:1 ethyl acetate-hexane (50 mL), washed with saturated sodium bicarbonate solution (50 mL) and brine (50 mL), dried over sodium sulfate, filtered, concentrated and purified by chromatography (12 g silica gel, 15% to 90% ethyl acetate-hexane) to afford 5-bromo-2-{(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl}phenyl acetate (114.5 mg, 100% yield) as a clear foam; Rf 0.11 (1:4 ethyl acetate-hexane).

Workup

  1. extractionextracted with 1:1 ethyl acetate-hexane (50 mL)
  2. washwashed with saturated sodium bicarbonate solution (50 mL) and brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by chromatography (12 g silica gel, 15% to 90% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-9b025cd5d9bf4c51ad4ed90d1a502a1d
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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