Water → HCID 66652808, compound

HRID 572553Notes

Reaction equation

HRID 572553 reaction equation
[NH2:1][CH:2]([CH:10]([CH3:12])[CH3:11])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[C:17]([F:23])[CH:16]=1)#[N:14].C([O-])(O)=O.[Na+].O>CN(C=O)C>[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:1][CH:2]([CH:10]([CH3:12])[CH3:11])[C:3]([O:5][C:6]([CH3:7])([CH3:9])[CH3:8])=[O:4])=[C:17]([F:23])[CH:16]=1)#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27831494-(Bromomethyl)-3-fluorobenzonitrileHCID 4532027Tert-butyl 2-amino-3-methylbutanoate

Product 1

HCID 66652808HCID 66652808, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of tert-butyl 2-amino-3-methylbutanoate (8.5 g, 0.05 mol) in dry DMF (50 mL) under nitrogen, was added 4-cyano-2-fluoro-benzyl bromide (FluoroChem Ltd, 9.4 g, 0.044 mol) and NaHCO3 (10.2 g, 0.12 mol). The resulting mixture was stirred at RT for 16 h. Water (70 mL) was added and the desired product was extracted with ethyl acetate (2×100 mL). The organic layer was washed with water (3×100 mL) and the solvent was dried over Na2SO4 and concentrated under vacuum. The resulted residue was purified by column chromatography using petroleum ether/ethyl acetate as eluent, affording of the title compound as colorless liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.77 (d, J=10.2 Hz, 1H), 7.67 (t, J=1.5 Hz, 1H), 3.85-3.79 (m, 2H), 2.72 (m, 1H), 2.49 (m, 1H), 1.81 (m, 1H), 1.37 (s, 9H), 0.86 (m, 6H).

Workup

  1. extractionthe desired product was extracted with ethyl acetate (2×100 mL)
  2. washThe organic layer was washed with water (3×100 mL)
  3. dry with materialthe solvent was dried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe resulted residue was purified by column chromatography

Sources & evidence

ORD record
ord-e80e0e9fc91740e9b8e0190d2e13c5e1
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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