Diisopropylethylamine → HCID 90051758, compound

HRID 2284723Notes

Reaction equation

HRID 2284723 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].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:47]([C:49]1[CH:50]=[C:51]([CH:53]=[CH:54][CH:55]=1)[NH2:52])#[CH:48].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CN(C)C=O>[C:47]([C:49]1[CH:50]=[C:51]([NH:52][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])[CH:53]=[CH:54][CH:55]=1)#[CH:48]

Participants

9

Reactant 6

HCID 81531DiisopropylethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 516892Sodium BicarbonateHCID 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 90051758HCID 90051758, compoundYield 20.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To N-Boc-N-methyl-L-alanine (2.03 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.81 g) and 1-hydroxybenzotriazole monohydrate (2.70 g), N,N-dimethylformamide (20 mL) was added at room temperature, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture, N,N-diisopropylethylamine (5.2 mL) and 3-ethynylaniline (1.17 g) were added at room temperature, and the mixture was stirred at the same temperature for 1 hour and 30 minutes. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 80 to 50% hexane in ethyl acetate) to obtain (S)-tert-butyl (1-((3-ethynylphenyl)amino)-1-oxopropan-2-yl)(methyl)carbamate (G1, 626 mg) as white solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour and 30 minutes
  2. customThe organic layer was separated
  3. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent, 80 to 50% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-c5609eeec68c4df5acdbef8257818133
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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