4-Methylmorpholine → HCID 7031902, compound

HRID 1171927Notes

Reaction equation

HRID 1171927 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6].[C:9]([NH:12][C@H:13]([C:21](O)=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:11])[CH3:10].CN1CCOCC1>ClCCl>[CH3:2][O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH:6][C:21](=[O:22])[C@H:13]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH:12][C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 74839N-Acetyl-L-phenylalanineHCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 7031902HCID 7031902, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

0.1 g of L-alanine methyl ester hydrochloride (0.7 mmol), 0.2 g of N-acetyl-L-phenylalanine (1 mmol) and 0.55 ml of N-methylmorpholine (5 mmol) are dissolved in 50 ml of dichloromethane and cooled to −10° C. 0.5 g of CPA from example 1 (50% in CH2Cl2; 0.8 mmol) is added slowly, and the mixture is stirred under cold conditions for 3 h and at room temperature for 72 h. The solution is concentrated by evaporation and extracted with ethyl acetate and 1N HCl solution, sat. NaHCO3, sat. NaCl and dist. water. The organic phase is dried over magnesium sulfate, filtered off and concentrated by evaporation. 0.18 g of the white N-acetyl-L-phenylalaninyl L-alanine methyl ester is obtained (88%).

Workup

  1. concentrationThe solution is concentrated by evaporation
  2. extractionextracted with ethyl acetate and 1N HCl solution, sat. NaHCO3, sat. NaCl and dist
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4ac3070532ed4cdb9d49d694dbca7bb3
Source dataset
uspto-grants-2010_11
Patent number
US07829736B2

Reaction notes

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