3-Mercaptopropionic Acid → HCID 53964521, compound
Reaction equation
[OH:1][CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:21])[C:12]([CH3:20])([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH3:13])=[CH:7][CH:6]=1.SC[CH2:24][C:25]([OH:27])=O.O.C1(C)C=CC([S:35](O)(=O)=O)=CC=1.[OH-].[Na+]>>[CH3:20][C:12]([N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)([CH3:13])[C:11]([C:8]1[CH:9]=[CH:10][C:5]([S:4][CH2:3][CH2:2][O:1][C:25](=[O:27])[CH2:24][SH:35])=[CH:6][CH:7]=1)=[O:21]Participants
Conditions
- Temperature
- 140 °C
Procedure
70 g (0.266 mol) of 1-[4-(2-hydroxyethylthio)-phenyl]-2-methyl-2-morpholin-4-yl-propan-1-one, 39 ml (0.452 mol) of 3-mercaptopropionic acid, and 47 g (0.249 mol) of p-toluenesulfonic acid monohydrate are mixed and stirred at 140° C. for 4 h. Then the solution is cooled to room temperature and neutralized with 1N NaOH. The crude product is extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (30:70) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.31 (s, 6H), 1.65 (t, 1H), 2.57 (t, 4H), 2.65 (t, 2H), 2.76 (dt, 2H), 3.26 (t, 2H), 3.70 (t, 4H), 4.33 (t, 2H), 7.33 (d, 2H), 8.51 (d, 2H).
Workup
- extractionThe crude product is extracted with ethyl acetate
- washwashed with saturated sodium chloride solution
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (30:70) as an eluent
Sources & evidence
- ORD record
- ord-2ac97d4bb4f748c695ecd9de5a10ef4c
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06022906
Reaction notes
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