Triethylamine → HCID 66677694, compound

HRID 2404301Notes

Reaction equation

HRID 2404301 reaction equation
Cl.[C:2]([O:6][C:7](=[O:11])[CH2:8][CH2:9][NH2:10])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.Br[CH2:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[C:24]#[N:25]>C(#N)C.O>[C:24]([C:23]1[CH:22]=[C:21]([CH:28]=[CH:27][CH:26]=1)[CH2:20][NH:10][CH2:9][CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:11])#[N:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 16218890Tert-butyl 3-aminopropanoate hydrochloride

Product 1

HCID 66677694HCID 66677694, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of β-alanine tert-butyl ester hydrochloride (7.1 g, 39.2 mmol) and triethylamine (14.2 mL, 107 mmol) in dry acetonitrile (100 mL) was added 3-(bromomethyl)benzonitrile (7.0 g, 35.7 mmol) in portions over 10 minutes at 0° C. After being stirred at RT for 5 hours, the reaction mixture was diluted with water (100 mL) and extracted with dichloromethane (2×100 mL) The organic layers were combined, dried using sodium sulphate and concentrated under reduced pressure. The residue was purified by flash chromatography affording the title compound as a pale yellow liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.75 (s, 1H), 7.66 (m, 2H), 7.50 (m, 1H), 3.71 (s, 2H), 2.64 (t, 2H), 2.32 (m, 2H), 1.37 (s, 9H).

Workup

  1. extractionextracted with dichloromethane (2×100 mL) The organic layers
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-979737f5abc6457fac581a1267fc8bbe
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

Loading…