Triethylamine → HCID 44403029, compound

HRID 1744058Notes

Reaction equation

HRID 1744058 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][C@@H:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.C1CN([P+](O[N:35]2N=[N:42][C:37]3C=CC=C[C:36]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:3]=[CH:4][C:5]([CH2:6][NH:7][C@@H:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([NH:42][CH2:37][C:36]#[N:35])=[O:11])=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 28354564HCID 28354564, compound

Product 1

HCID 44403029HCID 44403029, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (2S)-2-[(4-bromobenzyl)amino]-4-methylpentanoic acid (1.343 g, 4.62 mmol), PyBOP (2.65 g, 5.08 mmol), aminoacetonitrile hydrochloride (940 mg, 10.16 mmol) in dry DMF (30 mL) under dry nitrogen was added triethylamine (2.2 mL, 15.71 mmol) dropwise and the reaction was stirred for 4 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, 4/6 then 1/1) to afford (2S)-2-[(4-bromobenzyl)amino]-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, 4/6

Sources & evidence

ORD record
ord-4dd1855f5c474c04bcd416d3d8a3e911
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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