1-Octyne → HCID 131733952, compound

HRID 710355Notes

Reaction equation

HRID 710355 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].[CH:19]#[C:20][CH2:21]CCCCC.IC1C=CC(CCC#CC23CC4CC(CC(C4)C2[OH:48])C3)=CC=1.IC1C=C2C(=CC=1)CN([C:59]([C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1)([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)C1C=CC=CC=1)C2>>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:16]#[C:17][C:19]2[CH:73]=[CH:74][C:75]([CH2:76][CH2:77][C:72]#[C:59][C:66]3([OH:48])[CH2:67][CH2:68][CH2:69][CH2:70][CH2:71]3)=[CH:21][CH:20]=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

HCID 123701-OctyneHCID 115143851,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamateHCID 667262485-Iodo-2-tritylisoindolineHCID 66726898HCID 66726898, compound

Product 1

HCID 131733952HCID 131733952, compoundYield 62%

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 62% yield, as pale paste. 1H-NMR (CDCl3) 1.46 (s, 3H); 1.48 (s, 9H); 1.50 (s, 3H); 1.47-2.14 (m, 16H); 3.94-4.11 (m, 4H); 4.72 (5, 2H); 5.19 (s, 1H); 6.87 (d, 2H, J=8.85 Hz); 7.33 (d, 2H, J=8.79 Hz).

Sources & evidence

ORD record
ord-ccd589e4a2f6426eb2c238ba21c08dc7
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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