Methyl 3-mercaptopropionate → 5-Carbomethoxy-2-[(2-carbomethoxyethyl)thio]-pentanoic acid
Reaction equation
Br[CH:2]([CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:3]([OH:5])=[O:4].[CH3:13][O:14][C:15](=[O:19])[CH2:16][CH2:17][SH:18]>>[C:9]([CH2:8][CH2:7][CH2:6][CH:2]([S:18][CH2:17][CH2:16][C:15]([O:14][CH3:13])=[O:19])[C:3]([OH:5])=[O:4])([O:11][CH3:12])=[O:10]Participants
Procedure
5-Carbomethoxypentanoic acid (12), wherein alk is methyl, was reacted with thionyl chloride and then N-bromosuccinimide (NBS) followed by base hydrolysis to give 2-bromo-5-carbomethoxypentanoic acid (13). Compound (13) was reacted with methyl-3-mercaptopropionate (m=1, R1 '=H and R2 '=OCH3) to yield 5-carbomethoxy-2-[(2-carbomethoxyethyl)thio]-pentanoic acid (14). Compound (14) reacted first with diborane and then with dimethylsulfoxide and trifluoroacetic anhydride to afford 5-carbomethoxy-2-[(2-carbomethoxyethyl)thio]-pentanal (15). Compound (15) was reacted under Wittig conditions with tridecyltriphenylphosphonium ylid to yield methyl-5-[(2-carbomethoxyethyl)thio]-6(Z)-nonadecenoate (16) which was saponified to afford a compound of the formula (IV) wherein m is 1, R1 is hydrogen, and R2 is hydroxyl.
Sources & evidence
- ORD record
- ord-13c419d0e34f422a97467b4e2d1e2f69
- Source dataset
- uspto-grants-1988_10
- Patent number
- US04775662
Reaction notes
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