4-Methylmorpholine → HCID 13035201, compound

HRID 1171930Notes

Reaction equation

HRID 1171930 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[C:15]([NH:18][C@H:19]([C:27](O)=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:17])[CH3:16].CN1CCOCC1>CC(N(C)C)=O.CN(C)C=O>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:27](=[O:28])[C@H:19]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH:18][C:15](=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 74839N-Acetyl-L-phenylalanineHCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 13035201HCID 13035201, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

0.38 g of L-phenylalanine methyl ester hydrochloride (1.8 mmol), 0.37 g of N-acetyl-L-phenylalanine (1.7 mmol) and 5.0 ml of N-methylmorpholine (45.5 mmol) are dissolved in 30 ml of dimethylacetamide and cooled to 0° C. 5 ml of OPA, prepared as described in EP 0 527 442, example 1 (50% in dimethylformamide, molar amount not possible because the composition is not known) are then added. The mixture is stirred at 0° C. for another 1 h and at room temperature for 12 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. 0.55 g of the white N-acetyl-L-phenylalaninyl-L-phenylalanine methyl ester is obtained (87%).

Workup

  1. custom5 ml of OPA, prepared
  2. additionare then added
  3. concentrationThe solution is concentrated by evaporation
  4. extractionextracted with ethyl acetate and 1N HCl solution, sat. NaHCO3, sat. NaCl and dist
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered off
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b311925b41924ceb936b948fcb7f3ffc
Source dataset
uspto-grants-2010_11
Patent number
US07829736B2

Reaction notes

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