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Ethyl Acetate → (R)-2-(3-bromo-4-cyanophenylamino)-4-methylpentanamide

HRID 84804
Notes
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Reaction equation

HRID 84804 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:12][C@@H:13]([C:18]([NH2:20])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16].CCN(C(C)C)C(C)C.CCOC(C)=O>CS(C)=O.O>[Br:1][C:2]1[CH:9]=[C:8]([NH:12][C@H:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:18]([NH2:20])=[O:19])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 1189392-Bromo-4-fluorobenzonitrileHCID 56776963(R)-2-Amino-4-methylpentanamide hydrochloride

Product 1

HCID 67509372(R)-2-(3-bromo-4-cyanophenylamino)-4-methylpentanamideYield 60.3%

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent

Procedure

A solution of 2-bromo-4-fluorobenzonitrile (200 mg, 1.00 mmol), D-leucine amide hydrochloride (200 mg, 1.20 mmol) and DIEA (0.620 mL, 3.56 mmol) in DMSO (3 mL) was stirred at 100 C for 18 h. EtOAc and water were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted first with 30% EtOAc in hexane, then with 80% EtOAc to give (R)-2-(3-bromo-4-cyanophenylamino)-4-methylpentanamide (187 mg).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column
  5. washeluted first with 30% EtOAc in hexane

Sources & evidence

ORD record
ord-edd233d2d9d94267b1ccbb0294686228
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846928B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes