Triethylamine → N-(cyanomethyl)-4-methyl-2-(3-phenylphenyl)pentanamide

HRID 1060747Notes

Reaction equation

HRID 1060747 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:8]([OH:10])=O)[CH:2]=1.[NH2:21][CH2:22][C:23]#[N:24].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O.C(OCC)(=O)C>[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:8]([NH:24][CH2:23][C:22]#[N:21])=[O:10])[CH:2]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10901AminoacetonitrileHCID 2724699PyBOPHCID 218997772-Biphenyl-3-yl-4-methylpentanoic acid

Product 1

HCID 9815041N-(cyanomethyl)-4-methyl-2-(3-phenylphenyl)pentanamideYield 97.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution comprised of 2-biphenyl-3-yl-4-methylpentanoic acid (0.251 mg, 0.91 mmol), prepared as in Example 3, in DMF (5 mL) was treated with aminoacetonitrile (180 mg, 2 mmol), PyBOP (520 mg 1 mmol) and triethylamine (500 μL, 3 mmol). The mixture was stirred for 4 hours and then diluted with water (50 mL) and ethyl acetate (20 mL). The organic layer was separated, washed with 1 M saturated sodium bicarbonate solution, 1 M hydrochloric acid solution, water and brine, dried (MgSO4) and concentrated. The residue was recrystallized from 30% ethyl acetate in hexane to provide 2-biphenyl-3-yl-N-cyanomethyl-4-methylpentanamide (300 mg, 0.89 mmol). 1H NMR (DMSO-d6): 1.01 (d, 6H), 1.81-1.85 (m, 3H), 3.73 (dd, 1H), 4.35 (m, 2H), 7.12 (d, 1H), 7.24-7.37 (m, 8H) 8.31 (s, 1H). LCMS: 307.3 (M+H+).

Workup

  1. customThe organic layer was separated
  2. washwashed with 1 M saturated sodium bicarbonate solution, 1 M hydrochloric acid solution, water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized from 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b2de71c9837e492fa5d0113a5a0971d0
Source dataset
uspto-grants-2003_02
Patent number
US06525036B2

Reaction notes

Loading…