Triethylamine → HCID 86594551, compound

HRID 1744047Notes

Reaction equation

HRID 1744047 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([NH:6][C@@H:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:8]([OH:10])=O)=[CH:4][CH:3]=1.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:3]=[CH:4][C:5]([NH:6][C@@H:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:8]([NH:41][CH2:36][C:35]#[N:34])=[O:10])=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 69151219HCID 69151219, compound

Product 1

HCID 86594551HCID 86594551, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (2S)-2-(4-bromoanilino)-4-methylpentanoic acid (5.80 g, 20.28 mmol), PyBOP (11.08 g, 21.29 mmol), and aminoacetonitrile hydrochloride (3.75 g, 40.56 mmol) in dry DMF (150 mL) under dry nitrogen at 0° C. was added triethylamine (8.8 mL, 62.87 mmol) dropwise and the reaction was warmed to rt and stirred overnight. Aqueous sat. NaHCO3 was added and the product was extracted with ether (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 35/65 then 4/6) to afford (2S)-2-(4-bromoanilino)-N-(cyanomethyl)-4-methylpentanamide.

Workup

  1. extractionthe product was extracted with ether (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (EtOAc/Hex, 35/65

Sources & evidence

ORD record
ord-13d0da870a8840f484b7282b978649e2
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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