(2S)-1-tert-butoxycarbonyl-2(2-(1-allyloxycarbonylamino-isoquinolin-6-oxy)ethyl)-piperidine → 1-(N-cyclooctyl-gamma-tert-butyl-L-glutamyl)-2-(2-(1-allyloxycarbonylamino-isoquinolin-6-oxy)-ethyl)-piperidine

HRID 1070567Notes

Reaction equation

HRID 1070567 reaction equation
[CH:1]1([NH:9][C@H:10]([C:20]([OH:22])=O)[CH2:11][CH:12]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:15])=[O:14])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC([N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][C@H:31]1[CH2:36][CH2:37][O:38][C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)[C:45]([NH:49][C:50]([O:52][CH2:53][CH:54]=[CH2:55])=[O:51])=[N:44][CH:43]=[CH:42]2)=O)(C)(C)C>>[CH:1]1([NH:9][C@H:10]([C:20]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]2[CH2:36][CH2:37][O:38][C:39]2[CH:40]=[C:41]3[C:46](=[CH:47][CH:48]=2)[C:45]([NH:49][C:50]([O:52][CH2:53][CH:54]=[CH2:55])=[O:51])=[N:44][CH:43]=[CH:42]3)=[O:22])[CH2:11][CH:12]([C:16]([CH3:17])([CH3:18])[CH3:19])[C:13](=[O:14])[OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 20794986(2S)-1-tert-butoxycarbonyl-2(2-(1-allyloxycarbonylamino-isoquinolin-6-oxy)ethyl)-piperidineHCID 20794995N-cyclooctyl-gamma-tert-butyl-L-glutamic acid

Product 1

HCID 207949771-(N-cyclooctyl-gamma-tert-butyl-L-glutamyl)-2-(2-(1-allyloxycarbonylamino-isoquinolin-6-oxy)-ethyl)-piperidineYield 58%

Procedure

N-Cyclooctyl-γ-tert-butyl-L-glutamic acid (8a, 344 mg, 1.1 mmol) and 2-(2-(1-allyloxycarbonylamino-isoquinolin-6-oxy)-ethyl)-piperidine (1g, 391 mg, 1.1 mmol) were coupled, using the methodology described in Example 1i, providing 380 mg (58%) of the title compound as a colourless oil. ESI-MS: 651.3 (M+H)+. Rf (silica gel; dichloromethane/methanol, 9:1, v/v): 0.23.

Sources & evidence

ORD record
ord-eb3c6f24aac54ee98e6130be4c9011d4
Source dataset
uspto-grants-2005_06
Patent number
US06903107B1

Reaction notes

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