Acetic Acid → {(2S)-2-(3,4-Dichlorophenyl)-4-[3-(1-oxidothiomorpholin-4-yl)azetidin-1-yl]butyl}methylamine diacetate

HRID 749422노트

반응식

HRID 749422 반응식
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([C@H:11]([CH2:15][CH2:16][N:17]2[CH2:20][CH:19]([N:21]3[CH2:26][CH2:25][S:24][CH2:23][CH2:22]3)[CH2:18]2)[CH2:12][NH:13][CH3:14])[CH:7]=[CH:8][C:9]=1[Cl:10].OO.[C:29]([OH:32])(=[O:31])[CH3:30]>>[C:29]([O-:32])(=[O:31])[CH3:30].[NH4+:13].[C:29]([OH:32])(=[O:31])[CH3:30].[C:29]([OH:32])(=[O:31])[CH3:30].[Cl:3][C:4]1[CH:5]=[C:6]([C@H:11]([CH2:15][CH2:16][N:17]2[CH2:18][CH:19]([N:21]3[CH2:22][CH2:23][S:24](=[O:31])[CH2:25][CH2:26]3)[CH2:20]2)[CH2:12][NH:13][CH3:14])[CH:7]=[CH:8][C:9]=1[Cl:10]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 68979570[(2S)-2-(3,4-dichlorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylamine dihydrochloride

생성물 2

HCID 517165Ammonium AcetateHCID 86606877{(2S)-2-(3,4-Dichlorophenyl)-4-[3-(1-oxidothiomorpholin-4-yl)azetidin-1-yl]butyl}methylamine diacetate수율 49%

실험 절차

[(2S)-2-(3,4-Dichlorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylamine hydrochloride (see Method 1; 270 mg, 0.54 mmol) was dissolved in acetic acid and to the resultant solution was added hydrogen peroxide (0.05 mL of 35% aqueous solution, 0.54 mmol). The mixture was stirred at room temperature for 2.5 h and the solvent was removed by evaporation. The residue was dissolved in ethanol (50 mL) and to the resultant solution was added MP-Carbonate resin (0.86 g of 3.18 mmol/g polymer-bound resin). The mixture was stirred for 30 min and then filtered whereupon the solvent was removed by evaporation. The product was purified by reversed phase chromatography using a mixture of acetonitrile and 0.1 M ammonium acetate aq. There was obtained 140 mg (49%) of {(2S)-2-(3,4-Dichlorophenyl)-4-[3-(1-oxidothiomorpholin-4-yl)azetidin-1-yl]butyl}methylamine diacetate. 1H NMR (400 MHz, CDCl3): 1.6-1.8 (m, 2H), 1.9 (s, 6H), 2.3-2.4 (m, 1H), 2.4-2.5 (m, 7H), 2.7-3.0 (m, 10H), 3.1 (m, 1H), 3.6 (m, 2H), 7.0 (dd, 1H), 7.2 (d, 1H), 7.3 (d, 1H), 8.2 (s, 2H); LCMS: m/z 404 (M+1)+.

후처리

  1. customthe solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in ethanol (50 mL) and to the resultant solution
  3. additionwas added MP-Carbonate resin (0.86 g of 3.18 mmol/g polymer-bound resin)
  4. stirringThe mixture was stirred for 30 min
  5. filtrationfiltered whereupon the solvent
  6. customwas removed by evaporation
  7. customThe product was purified by reversed phase chromatography
  8. additiona mixture of acetonitrile

출처 및 근거

ORD 기록
ord-8b74534f63dd4021a4d3d23f5f8101ec
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402581B2

반응 노트

불러오는 중…