Oxalic Acid → 16-(p-Methylthiophenoxy)hexadeca-5,8,11,14-tetraynoic acid
Reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][C:14]#[C:15][CH2:16][C:17]#[C:18][CH2:19][S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)C.O1CCCCC1OC1CCCCO1.C(O)(=O)C(O)=O>C(OCC)(=O)C>[CH3:27][C:24]1[CH:25]=[CH:26][C:21]([S:20][CH2:19][C:18]#[C:17][CH2:16][C:15]#[C:14][CH2:13][C:12]#[C:11][CH2:10][C:9]#[C:8][CH2:7][CH2:6][CH2:5][C:4]([OH:28])=[O:3])=[CH:22][CH:23]=1Participants
Procedure
1.7 g of 16-(p-methylthiophenoxy)hexadeca-5,8,11,14-tetraynoic acid ethyl ester was mixed with 168 ml of the pH 6.7 buffer solution prepared in accordance with Example 1. The mixture was vigorously stirred and 16.24g of Sigma Lipase, Type VII, from Candida cylindracea were added, stirring was continued for 18 hours at room temperature; the reaction mixture was then transferred to a separatory funnel with 200 ml ethyl acetate and acidified with saturated solution of oxalic acid. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combinedorganic extract was dried over sodium sulfate and the solvent removed undervacuo. The residue was purified by TLC on silica gel with a Chromatotron using hexane-ethyl acetate (60:40) as the eluant, to yield 16-(p-methylthiophenoxy)hexadeca-5,8,11,14-tetraynoic acid, which was recrystallized from methylene chloride-hexane. M.P. 87°-88° C. (dec).
Workup
- customprepared in accordance with Example 1
- stirringstirring
- customThe organic layer was separated
- extractionthe aqueous layer extracted with ethyl acetate
- extractionThe combinedorganic extract
- dry with materialwas dried over sodium sulfate
- customthe solvent removed undervacuo
- customThe residue was purified by TLC on silica gel with a Chromatotron
Sources & evidence
- ORD record
- ord-d732c85232e14d02b19dd4a7577cc5bc
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04867915
Reaction notes
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