Triethylamine → (S)-Methyl 3-methyl-2-(6-(4-nitrophenyl)-1-oxoisoindolin-2-yl)butanoate

HRID 403699

Reaction equation

HRID 403699 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][C:4]=1[C:18]([O:20]C)=O.Cl.[CH3:23][O:24][C:25](=[O:31])[C@H:26]([CH:28]([CH3:30])[CH3:29])[NH2:27].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:29][CH:28]([CH3:30])[C@H:26]([N:27]1[CH2:2][C:3]2[C:4](=[CH:5][C:6]([C:9]3[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=3)=[CH:7][CH:8]=2)[C:18]1=[O:20])[C:25]([O:24][CH3:23])=[O:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 111190Methyl valinate hydrochlorideHCID 67306641Methyl 4-(bromomethyl)-4'-nitrobiphenyl-3-carboxylate

Product 1

HCID 131731440(S)-Methyl 3-methyl-2-(6-(4-nitrophenyl)-1-oxoisoindolin-2-yl)butanoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound of example 4 (1.54 g, 0.0044 mol) and L-valine methyl ester hydrochloride (0.813 g, 0.0048 mol) was taken in toluene (30 mL) in a round bottom flask. To this reaction mixture, triethyl amine (0.98 g, 0.0097 mol) was added and refluxed for 3-4 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate and concentrated to obtain an oily material, which was purified by column chromatography (silicagel, 30% ethyl acetate in petroleum ether).

Workup

  1. temperaturerefluxed for 3-4 h
  2. customAfter completion of the reaction
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto obtain an oily material, which
  7. customwas purified by column chromatography (silicagel, 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-c2862bf43348472a8229bbef8caf8c2b
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Linked notes

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