Water → HCID 66652808, compound

HRID 572570Notes

Reaction equation

HRID 572570 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 (Bachem, 6.3 g, 0.036 mol) in dry DMF (50 mL) under nitrogen, was added 4-cyano-2-fluoro-benzyl bromide (6.2 g, 0.029 mol) and NaHCO3 (6.09 g, 0.073 mol). The resulting mixture was stirred for 16 h at RT. Water (70 mL) was added and 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 the title compound as colorless liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.78 (d, J=10.2 Hz, 1H), 7.67 (t, J=1.5 Hz, 2H) 3.81 (m, 2H), 2.71 (m, 1H), 2.49 (m 1H), 1.81 (m, 1H), 1.37 (s, 9H), 0.88-0.84 (m, 6H).

Workup

  1. extractionextracted 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-5adae63dd96c48c48827a7b8af98c75b
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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