4-Ethynylheptan-4-ol → HCID 86628465, compound

HRID 2098526Notes

Reaction equation

HRID 2098526 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:10]([OH:20])[CH2:11][CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:21]([C:23]([OH:30])([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])#[CH:22]>>[F:16][C:15]([F:18])([F:17])[C:14]([NH:13][CH2:12][CH2:11][CH:10]([OH:20])[C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([C:22]#[C:21][C:23]([OH:30])([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH:3]=1)=[O:19]

Participants

3

Reactant 2

HCID 123838984-Ethynylheptan-4-olHCID 86628466N-(3-(3-bromo-4-methoxyphenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide

Product 1

HCID 86628465HCID 86628465, compound

Procedure

N-(3-(3-bromo-4-methoxyphenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide was coupled with 4-ethynylheptan-4-ol to give 2,2,2-trifluoro-N-(3-hydroxy-3-(3-(3-hydroxy-3-propylhex-1-ynyl)-4-methoxyphenyl)propyl)acetamide as a yellow oil. Yield (0.92 g, 55%): 1H NMR (400 MHz, DMSO-d6) δ 9.31 (t, J=5.0 Hz, 1H), 7.24-7.21 (m, 2H), 6.95 (d, J=9.2 Hz, 1H), 5.25 (d, J=4.8 Hz, 1H), 5.05 (s, 1H), 4.51-4.47 (m, 1H), 3.75 (s, 3H), 3.24-3.17 (m, 2H), 1.77-1.72 (m, 2H), 1.61-1.42 (m, 8H), 0.89 (t, J=7.0 Hz, 6H).

Sources & evidence

ORD record
ord-067a65677f9142dcb9fde2633c22a8a2
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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