2-(Aminomethyl)aniline → HCID 90052409, compound

HRID 2284660Notes

Reaction equation

HRID 2284660 reaction equation
[C:1]([N:8]([CH3:14])[C@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C.O>[NH2:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH:19][C:11](=[O:13])[C@@H:9]([N:8]([CH3:14])[C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH3:10]

Participants

9

Reactant 4

HCID 1780962-(Aminomethyl)anilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid

Product 1

HCID 90052409HCID 90052409, compoundYield 15.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of N-Boc-N-methyl-L-alanine (200 mg), 2-aminobenzylamine (240 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (755 mg) and 1-hydroxybenzotriazole monohydrate (603 mg) in N,N-dimethylformamide (4 mL), N,N-diisopropylethylamine (355 μL) was added at room temperature, and the mixture was stirred at the same temperature for 9 hours. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 75 to 50% hexane in ethyl acetate) to obtain oily (S)-tert-butyl (1-((2-aminobenzyl)amino)-1-oxopropan-2-yl)(methyl)carbamate (C9, 47 mg).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washwashed successively with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent, 75 to 50% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-d667c26b81cc411fa646ce89896f9a72
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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