4-Methylmorpholine → HCID 7031902, compound

HRID 1452788Notes

Reaction equation

HRID 1452788 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 1 N 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 1 N 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-1f60dfe513bb43a5b81d3a2ded8cd583
Source dataset
uspto-grants-2009_01
Patent number
US07473794B2

Reaction notes

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