Hydrochloric Acid → ethyl (RS)-alpha-[(morpholinosulphonyl)methyl]-hydrocinnamate
Reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]([CH:14]([CH2:20][S:21](Cl)(=[O:23])=[O:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C(Cl)Cl>[O:4]1[CH2:5][CH2:6][N:1]([S:21]([CH2:20][CH:14]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:23])=[O:22])[CH2:2][CH2:3]1Participants
Procedure
6.6 g (75.8 mmol) of morpholine are added dropwise at -10° to a solution of 6.23 g (21.4 mmol) of ethyl 2-benzyl-3-chlorosulphonyl-propionate (EPA 0236734) in 150 ml of methylene chloride. The solution is stirred at -10° for 1 hour and at 0° for 1 hour and subsequently acidified with 1N hydrochloric acid. The organic phase is then extracted with 50 ml of water, dried over sodium sulphate and evaporated. For purification, the residue (7.64 g) is chromatographed on 300 g of silica gel using methylene chloride as the eluent. There are obtained 6.78 g of ethyl (RS)-α-[(morpholinosulphonyl)methyl]-hydrocinnamate as a colourless oil; MS: 341 (M)+. This is converted into (S)-α-[(morpholinosulphonyl)methyl]hydrocinnamic acid by enzymatic hydrolysis using α-chymotrypsin in an analogous manner to that described in Example 1(d).
Workup
- extractionThe organic phase is then extracted with 50 ml of water
- dry with materialdried over sodium sulphate
- customevaporated
- customFor purification
- customthe residue (7.64 g) is chromatographed on 300 g of silica gel
Sources & evidence
- ORD record
- ord-6bbb31e86af74ffa9f51accdb3a983c7
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05688946
Reaction notes
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