Farnesol → HCID 71735432, compound

HRID 2167205Notes

Reaction equation

HRID 2167205 reaction equation
N1C=CC=[C:3]([NH:7][C:8](=[S:30])[O:9][CH2:10]/[CH:11]=[C:12](\[CH3:29])/[CH2:13][CH2:14]/[CH:15]=[C:16](\[CH3:28])/[CH2:17][CH2:18]/[CH:19]=[C:20](\[CH3:27])/[CH2:21]CC=C(C)C)C=1.C(O)/C=C(/CC/C=C(/CCC=C(C)C)\C)\C.CSN=C=O>>[CH3:3][NH:7][C:8](=[S:30])[O:9][CH2:10]/[CH:11]=[C:12](\[CH3:29])/[CH2:13][CH2:14]/[CH:15]=[C:16](\[CH3:28])/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:21])[CH3:27]

Participants

4

Reactant 3

HCID 445070FarnesolHCID 21933440MethylthioisocyanateHCID 86701128O-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl) pyridin-3-ylcarbamothioate

Product 1

HCID 71735432HCID 71735432, compoundYield 47%

Procedure

Similar to the preparation of 38a, the reaction of alcohol 5 with methyl thioisocyanate afforded the desired compound 43 in 47% yield (316 mg) as a viscous oil as a mixture of isomers: TLC Rf: 38 (10% EtOAc/hexanes): 1H NMR (300 MHz, CDCl3): δ 6.5 (br s, 0.3H), 6.2 (br s, 0.7H), 5.40-5.39 (m, 1H), 5.09-5.08 (m, 2H), 5.03-5.01 (d, 0.7H), 4.97-4.94 (d, 1.3H), 3.09-3.08 (d, 2H), 2.88-2.86 (d, 1H), 2.12-1.96 (m, 8H), 1.73-1.72 (m, 3H), 1.68 (m, 3H), 1.60 (m, 6H). 13CNMR (75 MHz, CDCl3): δ 143.1, 135.7, 131.6, 124.5, 123.8, 118.9, 118.2, 69.2, 67.6, 39.9, 39.8, 21.1, 30.0, 26.9, 26.4, 26.0, 18.0, 17.0, 16.9, 16.3.

Sources & evidence

ORD record
ord-31e5c8e5c9964d42918881205245dabd
Source dataset
uspto-grants-2015_06
Patent number
US09045403B2

Reaction notes

Loading…