Sodium Bicarbonate → (S)-1-((S)-2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-hydroxypropan-1-one

HRID 2189930Notes

Reaction equation

HRID 2189930 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C@:7]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:11]([C:12](=[O:33])[C@@H:13]([O:15][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH3:14])[N:10]=[C:9]([C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=2[F:41])[S:8]1)=[N+:2]=[N-:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([O-])(O)=O.[Na+]>C1COCC1>[N:1]([CH2:4][CH2:5][CH2:6][C@:7]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:11]([C:12](=[O:33])[C@@H:13]([OH:15])[CH3:14])[N:10]=[C:9]([C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=2[F:41])[S:8]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 86604833(S)-1-((S)-2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-(t-butyldiphenylsilyloxy)propan-1-one

Product 1

HCID 86604834(S)-1-((S)-2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-hydroxypropan-1-oneYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-1-((S)-2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-(t-butyldiphenylsilyloxy)propan-1-one (121 mg, 0.18 mmol) in THF (5 mL) at 0° C. was added TBAF (0.31 mL, 1M, 0.31 mmol). After stirring at 0° C. for 1 hour and at room temperature for 1 hour, the mixture was treated with saturated NaHCO3 and extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The brown oil was chromatographed (4:1 hexanes/ethyl acetate) to provide the product (4.1 mg, 53%) as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe brown oil was chromatographed (4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-c9f19f00cee44ab5b7fb238c60e54511
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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