Geranylgeraniol → (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl pyridin-4-ylcarbamate

HRID 2167202Notes

Reaction equation

HRID 2167202 reaction equation
N1C=CC=C(NC(=S)OC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)C=1.[CH2:31]([CH2:41]/[C:42](/[CH3:51])=[CH:43]/[CH2:44][CH2:45]/[C:46](/[CH3:50])=[CH:47]/[CH2:48][OH:49])/[CH:32]=[C:33](/[CH2:35][CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])\[CH3:34].[N:52]1[CH:57]=[CH:56][C:55]([N:58]=[C:59]=[O:60])=[CH:54][CH:53]=1>>[N:52]1[CH:57]=[CH:56][C:55]([NH:58][C:59](=[O:60])[O:49][CH2:48]/[CH:47]=[C:46](\[CH3:50])/[CH2:45][CH2:44]/[CH:43]=[C:42](\[CH3:51])/[CH2:41][CH2:31]/[CH:32]=[C:33](\[CH3:34])/[CH2:35][CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])=[CH:54][CH:53]=1

Participants

4

Reactant 3

HCID 5281365GeranylgeraniolHCID 11636796Pyridine, 4-isocyanato-HCID 86701128O-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl) pyridin-3-ylcarbamothioate

Product 1

HCID 71735434(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl pyridin-4-ylcarbamateYield 3%

Procedure

Similar to the preparation of 38a, the reaction of alcohol 1 with 4-pyridyl isocyanate afforded the desired compound 39 in 3% yield (10 mg) as a viscous oil. Column (DCM/MeOH); TLC Rf: 0.34 (10% MeOH/DCM); LCMS: MS (m/z): 411 (M+H).

Sources & evidence

ORD record
ord-d983189f62e34ff3978f07161012d7f4
Source dataset
uspto-grants-2015_06
Patent number
US09045403B2

Reaction notes

Loading…