Lipoic acid → HCID 86630289, compound
Reaction equation
[S:1]1[CH2:5][CH2:4][C@@H:3]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[S:2]1.Cl[CH2:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([OH:25])=[CH:22][CH:23]=2)[O:18][C:17](=[O:26])[CH:16]=1.N12CCCN=C1CCCCC2>C1C=CC=CC=1>[S:1]1[CH2:5][CH2:4][C@@H:3]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([OH:25])=[CH:22][CH:23]=3)[O:18][C:17](=[O:26])[CH:16]=2)=[O:11])[S:2]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a room temperature solution of (R)-(+)-1,2-dithiolane-3-pentanoic acid (2.66 g, 12.9 mmol) and 4-Chloromethyl-7-hydroxy-2H-chromen-2-one (1) (2.40 g, 11.4 mmol) in anhydrous benzene (160 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (3.8 mL, 25 mmol) in one portion. The reaction mixture was heated to 80° C. (oil bath temperature) for 1 h, cooled to room temperature, then quenched with aqueous 15% citric acid (200 mL). The resulting suspension was filtered, and the collected insoluble material was suspended in acetone (100 mL), sonicated for 60 s, then filtered onto a bed of silica gel (˜10 g). The suspension-sonication-filtration step was repeated a second time. Concentration of the filtrate under reduced pressure followed by flash column chromatography (1% MeOH in CH2Cl2) provided the desired product as a pale yellow powder (1.08 g, 25%).
Workup
- temperaturecooled to room temperature
- customquenched with aqueous 15% citric acid (200 mL)
- filtrationThe resulting suspension was filtered
- customsonicated for 60 s
- filtrationfiltered onto a bed of silica gel (˜10 g)
- filtrationThe suspension-sonication-filtration step
Sources & evidence
- ORD record
- ord-f140a8f62004432fac36112bafbf9a78
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09161931B2
Reaction notes
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