Sodium Hydroxide → HCID 15617539, compound
Reaction equation
[OH:1][CH:2]([CH:7]([S:27][CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)[C:3]([O:5]C)=[O:4].[OH-].[Na+]>CO>[OH:1][CH:2]([CH:7]([S:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)[C:3]([OH:5])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methyl 2-hydroxy-3-(2-carbomethoxyethylthio)-3-[2-(8-(2-furyl)octyl)phenyl]propanoate (0.068 g, 0.14 mmoles) was dissolved in methanol (2.0 ml), under argon, cooled to 0° C. and a 1N sodium hydroxide solution (0.54 ml) was added dropwise. The ice bath was removed and the reaction mixture permitted to warm to room temperature. After 5 hours, the methanol was evaporated and the residue diluted with water. The pH of the aqueous layer was adjusted to 2 with dilute hydrochloric acid. The acidic layer was then extracted with ethyl acetate, dried over magnesium sulfate, filtered and evaporated. The residue was flash chromatographed on silica gel to provide the desired product as a mixture of diastereomers, -log KB value 7.7.
Workup
- customThe ice bath was removed
- temperatureto warm to room temperature
- customthe methanol was evaporated
- additionthe residue diluted with water
- extractionThe acidic layer was then extracted with ethyl acetate
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customchromatographed on silica gel
Sources & evidence
- ORD record
- ord-cb1e8bee2f2a4851a35eb537ee837b3f
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04874792
Reaction notes
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