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 2421422Notes

Reaction equation

HRID 2421422 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 (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organics were washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated. The brown oil was chromatographed (4:1 hexanes/ethyl acetate) to provide the product (41 mg, 53%) as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined organics were washed with brine (20 mL)
  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-db5856293f8d4a97981c91a8fa34b38f
Source dataset
uspto-grants-2011_06
Patent number
US07956073B2

Reaction notes

Loading…