Triethylamine → 1-[(3S)-4-[(3-cyano-1-naphthoyl)(methyl)amino]-3-(3,4-dichlorophenyl)butyl)azetidin-3-yl methanesulfonate

HRID 749440ノート

反応式

HRID 749440 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][C@H:18]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:19][CH2:20][N:21]2[CH2:24][CH:23]([OH:25])[CH2:22]2)[CH3:16])=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C(Cl)Cl>[CH3:41][S:42]([O:25][CH:23]1[CH2:24][N:21]([CH2:20][CH2:19][C@@H:18]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:17][N:15]([C:13]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:14])[CH3:16])[CH2:22]1)(=[O:44])=[O:43]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 689772843-cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-(3-hydroxyazetidin-1-yl)butyl]-N-methyl-1-naphthamide

生成物 1

HCID 586835281-[(3S)-4-[(3-cyano-1-naphthoyl)(methyl)amino]-3-(3,4-dichlorophenyl)butyl)azetidin-3-yl methanesulfonate収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

3-Cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-(3-hydroxyazetidin-1-yl)butyl]-N-methyl-1-naphthamide (0.20 g, 0.41 mmol) was dissolved in CH2Cl2 and to the resultant solution was added triethylamine (0.17 mL, 0.41 mmol). The mixture was cooled to 0° C. before careful addition of methanesulfonyl chloride (0.03 mL, 0.41 mmol). The mixture was stirred with cooling for 30 min and then at room temperature for 1 h. The reaction mixture was diluted with CH2Cl2 and then washed with hydrochloric acid (1M), saturated NaHCO3 and then with brine. The organic solution was dried over MgSO4 and the solvent removed by evaporation. There was obtained 0.21 g (92%) of 1-[(3S)-4-[(3-cyano-1-naphthoyl)(methyl)amino]-3-(3,4-dichlorophenyl)butyl]azetidin-3-yl methanesulfonate as a solid. LCMS: m/z 560 (M+)+.

後処理

  1. temperaturewith cooling for 30 min
  2. washwashed with hydrochloric acid (1M), saturated NaHCO3
  3. dry with materialThe organic solution was dried over MgSO4
  4. customthe solvent removed by evaporation

出典と根拠

ORDレコード
ord-76a8e6a12702426abb51122c24dd523a
出典データセット
uspto-grants-2008_07
特許番号
US07402581B2

反応ノート

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