Triethylamine → HCID 68741257, compound

HRID 2354292Notes

Reaction equation

HRID 2354292 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)([CH3:20])[CH3:19].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([N:24]1[CH2:25][CH2:26][N:21]([CH:18]([CH3:20])[CH3:19])[CH2:22][CH2:23]1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 780131-IsopropylpiperazineHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanine

Product 1

HCID 68741257HCID 68741257, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 2-benzyloxycarbonylamino-2-methyl-propionic acid (2.37 g), 1-isopropylpiperazine (1.54 g), 1-hydroxybenzotriazole (1.49 g), 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride (2.88 g) and triethylamine (2.79 mL) in N,N-dimethylformamide (20 mL) was stirred at 50° C. overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, a saturated aqueous ammonium chloride solution, water, 0.5 mol/L aqueous sodium hydroxide solution, water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was washed with a mixed solvent of n-hexane and ethyl acetate (2/1), and dried under reduced pressure to give 1-(2-benzyloxycarbonylamino-2-methylpropionyl)-4-isopropyl-piperazine (1.83 g). This material was dissolved in methanol (20 mL). To the solution was added 10% palladium-carbon powder (0.60 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. The insoluble material was removed by filtration, and the solvent was removed under reduced pressure. The residue was crystallized from a mixed solvent of n-hexane and ethyl acetate, and the crystals were collected by filtration. The crystals were washed with n-hexane, and dried under reduced pressure to give the title compound (0.76 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materiala saturated aqueous ammonium chloride solution, water, 0.5 mol/L aqueous sodium hydroxide solution, water and brine successively, and dried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. washThe residue was washed with a mixed solvent of n-hexane and ethyl acetate (2/1)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-4b2430fe83b649ada6b101563e8c14b0
Source dataset
uspto-grants-2010_07
Patent number
US07750145B2

Reaction notes

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