4-Methylmorpholine → HCID 13035201, compound

HRID 1452789Notes

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

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 CPA from example 2 (50% in dimethylformamide, 1.9 mmol) are then added. The mixture is stirred at 0° 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. 0.53 g of the white N-acetyl-L-phenylalaninyl-L-phenylalanine methyl ester is obtained (84%).

Workup

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

Sources & evidence

ORD record: ord-b2dbce29f07b4a77889544644d8a2c1e
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473794B2

Reaction notes

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