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

HRID 1398329Notes

Reaction equation

HRID 1398329 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.FC(F)(F)S(O[CH2:37][CH2:38][C:39]([F:42])([F:41])[F:40])(=O)=O>C1COCC1>[C:1]1([C:7](=[N:14][CH:15]([CH2:37][CH2:38][C:39]([F:42])([F:41])[F:40])[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

5

Reactant 3

HCID 688171N-(Diphenylmethylene)glycine tert-butyl esterHCID 2724682Lithium diisopropylamideHCID 141328493,3,3-Trifluoropropyl trifluoromethanesulfonate

Product 1

HCID 86695928HCID 86695928, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 a 2M solution of LDA in THF (2.54 mL, 5.08 mmol) dropwise for 30 min. 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 (1×10 mL) and brine (1×10 mL), dried over sodium sulfate and then concentrated under reduced pressure. The crude oil was purified by silica gel column chromatography (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. LC/MS (ESI) m/e 391.9 [(M+H)+, calcd for C22H25F3NO2, 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 (1×10 mL) and brine (1×10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude oil was purified by silica gel column chromatography (2% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a52e4a318cbb43fea0f0aca136d4f01a
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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