N-(Diphenylmethylene)glycine tert-butyl ester → HCID 86695928, compound

HRID 870933Notes

Reaction equation

HRID 870933 reaction equation
[C:1]1([C:7](=[N:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.C1COCC1.CCCCCCC.C(C1C=CC=CC=1)C.FC(F)(F)S(O[CH2:57][CH2:58][C:59]([F:62])([F:61])[F:60])(=O)=O>C1COCC1>[C:1]1([C:7](=[N:14][CH:15]([CH2:57][CH2:58][C:59]([F:62])([F:61])[F:60])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 688171N-(Diphenylmethylene)glycine tert-butyl esterHCID 2724682Lithium diisopropylamideHCID 141328493,3,3-Trifluoropropyl trifluoromethanesulfonateHCID 22742125Tetrahydrofuran heptane ethylbenzol

Product 1

HCID 86695928HCID 86695928, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 2-((diphenylmethylene)amino)acetate (1 g, 3.39 mmol) in THF (20 ml) cooled to −78° C. under nitrogen atmosphere was added LDA, 2M in THF/heptane/ethylbenzene (2.54 ml, 5.08 mmol) dropwise for 30 mins. To this mixture was then added 3,3,3-trifluoropropyl trifluoromethanesulfonate (1.083 g, 4.40 mmol). The reaction was gradually warmed to rt and stirred for 4 h. The reaction mixture was quenched by addition of saturated aqueous ammonium chloride at 0° C. The reaction mixture was then extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with water and brine, dried over sodium sulfate and then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 2% ethyl acetate in hexane to afford tert-butyl 2-((diphenylmethylene)amino)-5,5,5-trifluoropentanoate (800 mg, 2.02 mmol, 60% yield) as a yellow oil. LCMS (ESI) m/e 391.9 [(M+H)+, calcd for C22H24F3NO2, 392.2]; LC/MS retention time (method E): tR=2.49 min.

Workup

  1. customThe reaction mixture was quenched by addition of saturated aqueous ammonium chloride at 0° C
  2. extractionThe reaction mixture was then extracted with ethyl acetate (3×10 mL)
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6d48bc4ef7424bfd93b117474a955710
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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