Potassium Phosphate, Tribasic → HCID 87827837, compound

HRID 2238673Notes

Reaction equation

HRID 2238673 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C@@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:14])[CH:8]=1)(=O)=O.[F:25][C:26]([F:36])([F:35])[C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:19]([O:18][C:16](=[O:17])[NH:15][C@H:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([N:32]2[CH2:33][CH2:34][N:29]([C:27](=[O:28])[C:26]([F:36])([F:25])[F:35])[CH2:30][CH2:31]2)[CH:8]=1)[CH3:14])([CH3:20])([CH3:21])[CH3:22]

Participants

7

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 516892Sodium BicarbonateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 7172020TrifluoroacetylpiperazineHCID 87540028HCID 87540028, compound

Product 1

HCID 87827837HCID 87827837, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of 306 mg of 3-{(1S)-1-[(t-butoxycarbonyl)amino]ethyl}phenyl trifluoromethanesulfonate (synthesized according to a method disclosed in J. Med. Chem. 2004, 47, 2887-2896), 181 mg of 2,2,2-trifluoro-1-piperazin-1-yl-ethanone, 47.6 mg of tris(dibenzylideneacetone)(chloroform)dipalladium (0), 49.4 mg of 2-(di-t-butylphosphino)biphenyl, 246 mg of tripotassium phosphate, and 4 mL of toluene, was stirred overnight at 100° C. After cooling the reaction mixture back to room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, and was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the insolubles were filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography, to obtain 277 mg of t-butyl((1S)-1-{3-[4-(trifluoroacetyl)piperazin-1-yl]phenyl}ethyl)carbamate [128-1] as a brown oily product.

Workup

  1. customsynthesized
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationthe insolubles were filtered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b75eba5ff5d5463cbed565cf2e38244c
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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