1-Octyne → tert-Butyl-5-((3-1-admantanyl-4-isopropoxyphenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate
Reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:16]#[CH:17])[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C#CCCCCCC.[C:27]12([C:37]3[CH:42]=[C:41](I)[CH:40]=[CH:39][C:38]=3[O:44][CH:45]([CH3:47])[CH3:46])[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[CH2:28]1)[CH2:34]2.IC1C=C2C(=CC=1)CN(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C2>>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:16]#[C:17][C:41]2[CH:40]=[CH:39][C:38]([O:44][CH:45]([CH3:47])[CH3:46])=[C:37]([C:27]34[CH2:36][CH:31]5[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]5)[CH2:28]3)[CH2:34]4)[CH:42]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]Participants
5
Reactant 4
Product 1
Procedure
When tert-butyl-5-ethynyl-2,2-dimethyl-1,3-dioxan-5-ylcarbamate was substituted for 1-octyne and the product of Step A was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 58% yield, as pale paste. 1H-NMR (CDCl3) 1.35 (d, 6H, J=6.01 Hz); 1.43 (s, 3H); 1.47 (s, 9H); 1.48 (s, 3H); 1.74 (s, 6H); 2.06 (s, 9H); 3.99 (d, 2H, J=11.45 Hz); 4.08 (d, 2H, J=11.51 Hz); 4.59-4.64 (m, 1H); 5.17 (broad s, 1H); 6.72 (d, 1H, J=8.61 Hz); 7.21 (dd, 1H, J=2.08, 8., Hz); 7.25 (d, 1H, J=2.09 Hz).
Sources & evidence
- ORD record
- ord-c9a461644560441f910d8d5bfe55e3bb
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
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