4-Methylmorpholine → HCID 131718917, compound

HRID 1608524Notes

Reaction equation

HRID 1608524 reaction equation
Cl.COC(=O)[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].CN1CC[O:19][CH2:18]C1.[C:22]([NH:25][C@H:26]([C:31]([OH:33])=O)[CH2:27][CH:28]([CH3:30])[CH3:29])(=[O:24])[CH3:23].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(CC)CC)C>CN(C=O)C.O>[CH:18]([C:8]1([CH:9]=[CH:10][CH:11]=[CH:12][CH2:13]1)[CH2:7][CH2:5][NH:6][C:31](=[O:33])[C@H:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[NH:25][C:22](=[O:24])[CH3:23])=[O:19]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 70912N-Acetyl-L-leucineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Product 1

HCID 131718917HCID 131718917, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 100 ml of DMF was dissolved 5.0 g of L-phenylalanine methyl ester hydrochloride, and 2.4 g of N-methylmorpholine was added thereto. To the solution were added 4.0 g of N-acetyl-L-leucine, 5.0 g of 1-hydroxybenzotriazole, and 5.5 g of 1-ethyl-3-(3-diethylaminopropyl)carbodiimide hydrochloride, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with a 10% citric acid solution, a saturated brine, a saturated sodium bicarbonate solution, and a saturated brine and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by medium-pressure column chromatography on silica gel to obtain 6.7 g of the titled compound as a colorless crystal.

Workup

  1. additionwas added
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed successively with a 10% citric acid solution
  5. dry with materiala saturated brine, a saturated sodium bicarbonate solution, and a saturated brine and dried over sodium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe residue was purified by medium-pressure column chromatography on silica gel

Sources & evidence

ORD record
ord-2696e059ab8f4e8f85796e7fca599811
Source dataset
uspto-grants-1995_03
Patent number
US05395824

Reaction notes

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