Propan-2-yl 2-aminoacetate → Isopropyl 2-((diphenylmethylene)amino)-5-oxo-4-(2,3,6-trifluorophenyl)hexanoate

HRID 706380Notes

Reaction equation

HRID 706380 reaction equation
[NH2:1][CH2:2][C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4].[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=1[C:18](=[CH2:22])[C:19](=[O:21])[CH3:20].[C:23](O[Li])([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[C:23]1([C:26](=[N:1][CH:2]([CH2:22][CH:18]([C:11]2[C:12]([F:17])=[CH:13][CH:14]=[C:15]([F:16])[C:10]=2[F:9])[C:19](=[O:21])[CH3:20])[C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:25]=[CH:22][CH:18]=[CH:19][CH:24]=1

Participants

5

Reactant 3

HCID 13820629Propan-2-yl 2-aminoacetateHCID 898150313-(2,3,6-Trifluorophenyl)but-3-en-2-oneHCID 178506942HCID 178506942, compound

Product 1

HCID 89814926Isopropyl 2-((diphenylmethylene)amino)-5-oxo-4-(2,3,6-trifluorophenyl)hexanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diphenylidene isopropyl glycinate (2.0 g, 7.0 mmol) and 31 (1.4 g, 7.0 mmole) were dissolved in THF (10 ml). The solution was cooled to −10° C. tert-BuOLi (0.56 g, 7.0 mmole) was charged into the solution in several portions. The reaction was warmed up to room temperature slowly and stirred overnight. After quenched by addition of aqueous NH4Cl, the solvents were removed by distillation under vacuum. The residue was subjected to silica chromatography column eluted by hexane and EtOAc yielding 32 (3.0 g, 89%) as an oil, which was directly used in the next step.

Workup

  1. additionwas charged into the solution in several portions
  2. customAfter quenched by addition of aqueous NH4Cl
  3. customthe solvents were removed by distillation under vacuum
  4. washeluted by hexane and EtOAc yielding 32 (3.0 g, 89%) as an oil, which

Sources & evidence

ORD record
ord-48e019fd89de4ef187d66fec5833f2f7
Source dataset
uspto-grants-2015_11
Patent number
US09174989B2

Reaction notes

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