1-Octyne → tert-Butyl-5-((4-(N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)sulfam-oyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710342Notes

Reaction equation

HRID 710342 reaction equation
[C:1]([C:3]1([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1)#[CH:2].C#CCCCCCC.Br[C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH:37][CH:38]2[CH2:43][CH2:42][CH:41]3[CH2:44][CH:39]2[C:40]3([CH3:46])[CH3:45])(=[O:36])=[O:35])=[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:14]([O:13][C:12](=[O:18])[NH:11][C:3]1([C:1]#[C:2][C:28]2[CH:29]=[CH:30][C:31]([S:34](=[O:35])(=[O:36])[NH:37][CH:38]3[CH2:43][CH2:42][CH:41]4[CH2:44][CH:39]3[C:40]4([CH3:45])[CH3:46])=[CH:32][CH:33]=2)[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 4

HCID 123701-OctyneHCID 115143851,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamateHCID 666149414-Bromo-N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)benzene sulfonamideHCID 667262485-Iodo-2-tritylisoindoline

Product 1

HCID 131733945tert-Butyl-5-((4-(N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)sulfam-oyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateYield 46%

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 46% yield, as a creamy paste. 1H-NMR (CDCl3) 0.85 (s, 3H); 1.1 (s, 3H); 1.44 (s, 3H); 1.46 (s, 9H); 1.48 (s, 3H); 1.63-1.65 (m, 2H); 1.79-1.86 (m, 5H); 2.05-2.08 (m, 1H); 2.27-2.32 (m, 1H); 2.89 (tr, 2H, J=6.59 Hz); 4.0-4.13 (m, 4H); 4.6 (broad s, 1H); 5.23 (s, 1H); 7.52 (d, 2H, J=8.25 Hz); 7.75 (d, 2H, J=8.46 Hz).

Sources & evidence

ORD record
ord-fdad6b56e7cd450daea112dfbf0962a5
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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