1-Octyne → HCID 131733954, compound

HRID 710358Notes

Reaction equation

HRID 710358 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.Br[C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([C:42]34[CH2:51][CH:46]5[CH2:47][CH:48]([CH2:50][CH:44]([CH2:45]5)[CH2:43]3)[CH2:49]4)[CH:35]=2)=[CH:30][CH:29]=1.IC1C=C2C(=CC=1)CN(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C2>>[C:42]12([C:36]3[CH:35]=[C:34]([C:31]4[CH:32]=[CH:33][C:28]([C:17]#[C:16][C:8]5([NH:7][C:6](=[O:18])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]5)=[CH:29][CH:30]=4)[CH:39]=[CH:38][C:37]=3[O:40][CH3:41])[CH2:49][CH:48]3[CH2:47][CH:46]([CH2:45][CH:44]([CH2:50]3)[CH2:43]1)[CH2:51]2

Participants

5

Reactant 4

HCID 123701-OctyneHCID 115143851,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamateHCID 667262485-Iodo-2-tritylisoindolineHCID 66726624HCID 66726624, compound

Product 1

HCID 131733954HCID 131733954, compoundYield 35%

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 35% yield, as pale paste. 1H-NMR (CDCl3) 1.47 (s, 3H); 1.48 (s, 9H); 1.5 (s, 3H); 1.77 (broad s, 6H); 2.07 (broad s, 3H); 2.12 (s, 6H); 3.86 (s, 3H); 4.00 (d, 2H, J=11.38 Hz); 4.10 (d, 2H, J=11.45 Hz); 5.20 (s, 1H); 6.9 (d, 1H, J=8.46 Hz); 7.28-7.5 (s, 6H).

Sources & evidence

ORD record
ord-9bcea2d22bf7482cb83ffa9ae7e6089b
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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