2-(Isothiocyanatomethyl)furan → O-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl) (furan-2-ylmethyl)carbamothioate

HRID 2167200Notes

Reaction equation

HRID 2167200 reaction equation
N1[CH:6]=[CH:5][CH:4]=[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][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])C=1.C(C/C(/C)=C/CC/C(/C)=C/[CH2:48][OH:49])/C=C(/CCC=C(C)C)\C.O1C=CC=C1CN=C=S>>[O:49]1[CH:48]=[CH:6][CH:5]=[C:4]1[CH2:3][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][CH2:22][CH:23]=[C:24]([CH3:25])[CH3:26]

Participants

4

Reactant 3

HCID 783802-(Isothiocyanatomethyl)furanHCID 5281365GeranylgeraniolHCID 86701128O-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl) pyridin-3-ylcarbamothioate

Product 1

HCID 86701129O-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl) (furan-2-ylmethyl)carbamothioateYield 23%

Procedure

Similar to the preparation of 38a, the reaction of alcohol 1 with 2-furanylmethyl isothiocyanate afforded the desired compound 38b in 23% yield (55 mg) as a viscous oil. Column (EtOAc/Hexane); TLC Rf: 0.65 (20% EtOAc/hexanes); 1H NMR (300 MHz, CDCl3): δ 7.35 (s 1H), 6.35 (m, 1H), 5.15 (m, 3H), 5.04 (d, 0.4H), 4.95 (d, 0.6H), 4.75 (d, 0.6H), 4.42 (d 0.4H), 2.14-1.94 (m, 12H), 1.73 (s, 3H), 1.68 (s, 3H), 1.60 (s, 9H); LCMS: MS (m/z): 430.2 (M+H).

Sources & evidence

ORD record
ord-4b465da85c5c48c99c595dd7cf00272c
Source dataset
uspto-grants-2015_06
Patent number
US09045403B2

Reaction notes

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