Water → HCID 58134627, compound

HRID 444772Notes

Reaction equation

HRID 444772 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([NH:9][CH:10]=[C:11]([C:17](=[O:28])[C:18]2[CH:23]=[C:22]([F:24])[C:21]([F:25])=[C:20]([F:26])[C:19]=2F)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8][CH2:7][CH2:6][CH2:5]1.[H-].[Na+].O>C1COCC1>[F:26][C:20]1[CH:19]=[C:18]2[C:23](=[C:22]([F:24])[C:21]=1[F:25])[N:9]([C:4]1([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6][CH2:7][CH2:8]1)[CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]2=[O:28]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 178471958HCID 178471958, compound

Product 1

HCID 58134627HCID 58134627, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an iced solution of ethyl 3-[1-(2-hydroxyethyl)-cyclopentylamino]-2-(2,3,4,5-tetrafluorobenzoyl)acrylate (22.7 g, 56.3 mmol) in THF (200 mL) was added NaH (3.60 g, 90.0 mmol), and the mixture was stirred at room temperature for 1 hour. Water was added to the mixture portionwise at 0° C. The resulting mixture was extracted with ethyl acetate, and the combined organic extracts were concentrated in vacuo. Flash chromatography (AcOEt:Hexane=2:1) of the residue give the title compound as a colorless solid (14.1 g, 65%). 1H-NMR (400 MHz, DMSO-d6) δ 1.27 (3H, t, J=7.3 Hz), 1.53-1.75 (4H, m), 2.10-2.26 (4H, m), 2.31-2.44 (2H, m), 4.23 (2H, q, J=7.3 Hz), 4.55-4.60 (1H, m), 7.99-8.07 (1H, m), 8.80 (1H, s).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. concentrationthe combined organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-984c1d40255b4d5abbe256f50ae1a72e
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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