HCID 14770881, compound → 2-(Sulfanylmethyl)pentanedioic acid
Reaction equation
C([S:9][CH2:10][CH:11]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:12]([OH:14])=[O:13])(=O)C1C=CC=CC=1>COCCN>[SH:9][CH2:10][CH:11]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:12]([OH:14])=[O:13]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
S-Benzoyl-2-mercaptomethylglutaric acid (2 g, 7.08 mmol) was added with stirring to 2-methoxyethylamine (20 mL) kept at 0°-5° C. The resulting solution was stirred for 2 hours at 0° C. and at 30° C. for 1 hour. The thick viscous liquid was evaporated at 60° C. under vacuum to a transparent gel. The residue was dissolved in oxygen-free water (40 mL) and extracted with three portions of EtOAc. The aqueous fraction was acidified with 18% HCl and reextracted with EtOAc. The EtOAc layer was dried over Na2SO4 and evaporated to a thick gel. The residue was dissolved in a mixture of EtOAc/hexane and cooled to -18° C. overnight. The white precipitate formed was collected by filtration, washed and dried under vacuum at room temperature to yield, 1.16 g (91.8%) of the captioned product (mp 75° C.)
Workup
- customkept at 0°-5° C
- customThe thick viscous liquid was evaporated at 60° C. under vacuum to a transparent gel
- dissolutionThe residue was dissolved in oxygen-free water (40 mL)
- extractionextracted with three portions of EtOAc
- dry with materialThe EtOAc layer was dried over Na2SO4
- customevaporated to a thick gel
- dissolutionThe residue was dissolved in a mixture of EtOAc/hexane
- temperaturecooled to -18° C. overnight
- customThe white precipitate formed
- filtrationwas collected by filtration
- washwashed
- customdried under vacuum at room temperature
- customto yield
Sources & evidence
- ORD record
- ord-9b510f8a55764c03b9ca0ec94f7244e8
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04927966
Reaction notes
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