Water → HCID 10001566, compound
Reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CC(C)([O-])C.[K+].S(O[CH:25]([CH2:37][CH2:38][CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1)[CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1)(C1C=CC(C)=CC=1)(=O)=O.O>CN(C)C=O.O1CCCC1>[O:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH:31]1[O:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:25]([CH2:37][CH2:38][CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1)[S:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]Participants
Procedure
To a solution of 0.125 ml (1.1 mmol) ethyl 2-mercaptoacetate in 2.4 ml dimethylformamide is added 0.68 ml (1.1 mmol) of 1.61M potassium t-butoxide in tetrahydrofuran. The solution is stirred at room temperature for 30 min and then a solution of 0.402 g (0.87 mmol) 5-tosyloxy-8-(3-pyridyl)-1-(2-tetrahydropyranyloxy)-octane in 1 ml dimethylformamide is added. The mixture is stirred at room temperature for 18 h, poured into water and then extracted with ethyl acetate. The organic phase is washed with water, brine, dried, filtered and evaporated to give an orange oil which is purified by preparative thin layer chromatography using ether/hexane (4:1) as the eluent to give ethyl 8-(2-tetrahydropyranyloxy)-4-[3-(3-pyridyl)propyl]-3-thia-octanoate; IR (CH2Cl2): 1729, 1134 cm-1.
Workup
- stirringThe mixture is stirred at room temperature for 18 h
- extractionextracted with ethyl acetate
- washThe organic phase is washed with water, brine
- customdried
- filtrationfiltered
- customevaporated
- customto give an orange oil which
- customis purified by preparative thin layer chromatography
Sources & evidence
- ORD record
- ord-f3af1ae3bd5c4a72b6665932791a8225
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05153214
Reaction notes
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