4-Methylmorpholine → HCID 13035201, compound

HRID 1452790Notes

Reaction equation

HRID 1452790 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 22.4%

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 1.6 ml of N-methylmorpholine (14.6 mmol) are dissolved in 30 ml of dimethylacetamide and cooled to 0° C. 1.2 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 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. 0.14 g of the white N-acetyl-L-phenylalaninyl-L-phenylalanine methyl ester is obtained (22%).

Workup

  1. custom1.2 ml of OPA, prepared
  2. additionare then added
  3. concentrationThe solution is concentrated by evaporation
  4. extractionextracted with ethyl acetate and 1 N 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-6b9d39603152420fba5a14f08ebe4bec
Source dataset
uspto-grants-2009_01
Patent number
US07473794B2

Reaction notes

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