Ammonia → [[(1-Methyl-1-(morpholinocarbonyl)ethyl]sulfonyl]methyl]hydrocinnamamide

Analogously to the procedure described by Wang et al. in Synthesis 1989, 37 a mixture of 15.34 g (40mmol) of (S)-α-[[[(1-methyl-1-(morpholinocarbonyl)ethyl]sulfonyl]methyl]hydrocinnamic acid, 9.29 g (40 mmol) of dicyclohexylcarbodiimide and 6.89 g (50 mmol) of HOBT in 160 ml of methylene chloride and 40 ml of dimethylformamide was stirred at room temperature for 4 hours. Thereafter, the reaction mixture was filtered, the yellowish solution obtained was diluted with 200 ml of methylene chloride and cooled to 0°. Ammonia was conducted into this solution until it was saturated. The suspension obtained was stirred at room temperature for 1 hour. Subsequently, the solid formed was filtered off under suction and washed with 100 ml of methylene chloride. The yellow coloured filtrate was then washed twice with in each case 200 ml of water and twice with 200 ml of saturated sodium chloride solution. The wash solutions were extracted with 500 ml of methylene chloride. The combined organic phases were dried over sodium sulphate and thereafter evaporated under reduced pressure. For purification, the yellowish crude product obtained (15.3 g) was chromatographed on 1.3 kg of silica gel using a 4:1 mixture of ethyl acetate and hexane as the eluent. There were obtained 13.6 g of (S)-α-[[[(1-methyl-1-(morpholinocarbonyl)ethyl]sulfonyl]methyl]hydrocinnamamide as a colourless powder, MS: 383 (M+H)+.

1. customAnalogously to the procedure described by Wang et al. in Synthesis 1989, 37
2. filtrationThereafter, the reaction mixture was filtered
3. customthe yellowish solution obtained
4. temperaturecooled to 0°
5. customThe suspension obtained
6. stirringwas stirred at room temperature for 1 hour
7. customSubsequently, the solid formed
8. filtrationwas filtered off under suction
9. washwashed with 100 ml of methylene chloride
10. washThe yellow coloured filtrate was then washed twice with in each case 200 ml of water and twice with 200 ml of saturated sodium chloride solution
11. extractionThe wash solutions were extracted with 500 ml of methylene chloride
12. dry with materialThe combined organic phases were dried over sodium sulphate
13. customevaporated under reduced pressure
14. customFor purification
15. customthe yellowish crude product obtained (15.3 g)
16. customwas chromatographed on 1.3 kg of silica gel using
17. additiona 4:1 mixture of ethyl acetate and hexane as the eluent

ORD record

ord-2043393707ab4bbb8d5af83618622c12

Source dataset

uspto-grants-1995_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05393875