HCID 54196676, compound → HCID 56631144, compound
Reaction equation
[CH3:1][CH:2]([CH3:12])[CH2:3][C:4](=[CH:8][CH:9]([CH3:11])[CH3:10])[C:5]([OH:7])=[O:6].[C:13]([OH:16])(=[S:15])[CH3:14]>>[C:13]([S:15][CH:8]([CH:4]([CH2:3][CH:2]([CH3:12])[CH3:1])[C:5]([OH:7])=[O:6])[CH:9]([CH3:11])[CH3:10])(=[O:16])[CH3:14]Participants
Procedure
E and Z 2-(2-methylpropyl)-4-methyl-pent-2-enoic acid (7 g) in thioacetic acid (50 ml) was heated at 100° C. under reflux for 72 h. The excess thioacetic acid was removed in vacuo and the residue dissolved in dichloromethane which was extracted with aqueous saturated sodium hydrogen carbonate (3×200 ml). The aqueous phase was separated, acidified to pH1 with concentrated hydrochloric acid and extracted with fresh dichloromethane. The organic extract was dried over sodium sulphate and concentrated in vacuo to a gum which was chromatographed on silica in 15% ethyl acetate in dichloromethane to afford 2-(RS)-(1-(RS)-S-Acetyl mercapto-2-methylpropyl)-4-methyl pentanoic acid (2.0 g) as a colourless oil δ(CDCl3) 0.86-1.08 (12H, m, 2×CH(CH3)2); 1.32-1.46 (1H, m, CH); 1.48-1.78 (2H, m, CH2); 1.92-2.12 (1H, m, CH); 2.36 and 2.39 (3H, each s, CH3COS); 2.65 and 2.9 (1H, each m, CH); 3.65 and 3.78 (1H, each m, CHS).
Workup
- temperatureunder reflux for 72 h
- customThe excess thioacetic acid was removed in vacuo
- dissolutionthe residue dissolved in dichloromethane which
- extractionwas extracted with aqueous saturated sodium hydrogen carbonate (3×200 ml)
- customThe aqueous phase was separated
- extractionextracted with fresh dichloromethane
- extractionThe organic extract
- dry with materialwas dried over sodium sulphate
- concentrationconcentrated in vacuo to a gum which
- customwas chromatographed on silica in 15% ethyl acetate in dichloromethane
Sources & evidence
- ORD record
- ord-d53956cf50da421a9db189cffdc237f7
- Source dataset
- uspto-grants-1987_07
- Patent number
- US04681966
Reaction notes
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