Amyl isothiocyanate → O-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl) butylcarbamothioate
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/CO)/C=C(/CCC=C(C)C)\C.C(N=C=S)CCCC>>[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]([CH3:26])[CH3:25])[CH2:4][CH2:5][CH3:6]Participants
4
Procedure
Similar to the preparation of 38a, the reaction of alcohol 1 with pentyl isothiocyanate afforded the desired compound 10e in 60% yield (135 mg) as a viscous oil. Column (EtOAc/Hexane); TLC Rf: 0.70 (10% EtOAc/hexanes); LCMS: MS (m/z): 406.1 (M+H).
Sources & evidence
- ORD record
- ord-7445d9dbd2d943a6af136cf962a8430c
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045403B2
Reaction notes
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