L-Isoleucine, ethyl ester → N-(12-Methoxy-1-oxododecyl)-L-isoleucine, Ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:11])[C@H:5]([C@H:7]([CH2:9][CH3:10])[CH3:8])[NH2:6])[CH3:2].[C:12]([O:15][CH2:16][CH3:17])(=O)C.[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[CH3:12][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:7][CH2:5][C:4]([NH:6][C@H:5]([C:4]([O:3][CH2:1][CH3:2])=[O:11])[C@H:7]([CH2:9][CH3:10])[CH3:8])=[O:3]Participants
3
Procedure
The title compound was prepared by the method of Example 14 using the title product of Example 44 (1.1 g, 4 mmol) instead of benzylamine. Chromatography of the crude residue on silica gel using 50--50 ethyl acetate-heptane as eluant gave the title compound (875 mg) as a white powder, m.p. 36.4°-38.1° C. (DSC). The structure was supported by NMR, infrared spectroscopy, optical rotation ([α]36525 +81.9°, CHCl3), elemental analysis, and mass spectroscopy.
Sources & evidence
- ORD record
- ord-b9b3aa9a5f5f48789c0f27baa0a671b5
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05599947
Reaction notes
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