4-Methylmorpholine → HCID 18659618, compound

HRID 1608525Notes

Reaction equation

HRID 1608525 reaction equation
Cl.C[O:3][C:4](=O)[C@H:5]([CH2:7][CH2:8][CH2:9][CH3:10])[NH2:6].CN1CCOCC1.[CH2:19]([O:26][C:27]([NH:29][C@H:30]([C:38]([OH:40])=O)[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N=C=NCCCN(CC)CC)C>C(Cl)Cl.O>[CH:4]([CH:5]([NH:6][C:38](=[O:40])[C@H:30]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[NH:29][C:27]([O:26][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:28])[CH2:7][CH2:8][CH2:9][CH3:10])=[O:3]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 99645131-Ethyl-3-(3-diethylaminopropyl)carbodiimideHCID 14039065methyl (2S)-2-aminohexanoate hydrochloride

Product 1

HCID 18659618HCID 18659618, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In 50 ml of methylene chloride was dissolved 1.8 g of L-norleucine methyl ester hydrochloride, and 1.1 ml of N-methylmorpholine was added to the solution. To the solution were further added 3.0 g of N-benzyloxycarbonyl-L-phenylalanine and 1.9 g of 1-ethyl-3-(3-diethylaminopropyl)carbodiimide, 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 organic layer 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 to obtain 4.1 g of the titled compound.

Workup

  1. additionwas added to the solution
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer 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

Sources & evidence

ORD record
ord-ea84a4c9d7e944f39ef23346df770e47
Source dataset
uspto-grants-1995_03
Patent number
US05395824

Reaction notes

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