Triethylamine → 2-(2-bromobenzyl)-N-(cyanomethyl)-4-methylpentanamide

HRID 1744072Notes

Reaction equation

HRID 1744072 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][CH:5]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:6]([OH:8])=O.C1CN([P+](O[N:34]2N=[N:41][C:36]3C=CC=C[C:35]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.NCC#N.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][CH:5]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:6]([NH:41][CH2:36][C:35]#[N:34])=[O:8]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 222362182-(2-Bromobenzyl)-4-methylpentanoic acid

Product 1

HCID 222361892-(2-bromobenzyl)-N-(cyanomethyl)-4-methylpentanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-(2-bromobenzyl)-4-methylpentanoic acid (1.248 g, 4.38 mmol), PyBOP (3.12 g, 6.0 mmol), aminoacetonitrile hydrochloride (1.11 g, 12.0 mmol) in dry DMF (30 mL) under dry nitrogen was added triethylamine (1.9 mL, 18.53 mmol) dropwise and the reaction was stirred for 2.5 hours. Aqueous Sat. NaHCO3 was added and the product, extracted with Et2O (2×), dried on Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 3/7) to afford 2-(2-bromobenzyl)-N-(cyanomethyl)-4-methylpentanamide.

Workup

  1. extractionthe product, extracted with Et2O (2×)
  2. customdried on Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (EtOAc/Hex, 3/7)

Sources & evidence

ORD record
ord-5466c559452b4bc4b1ba43ce4fd0b1de
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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