Dimethylformamide → Methyl 5-chloro-2-(3-((methylsulfonyl)oxy)azetidin-1-yl)nicotinate

HRID 72431

反応式

HRID 72431 の反応式
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([OH:16])[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.CN(C)C=O.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:13][CH:14]([O:16][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:15]2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 8471Triethylamine2 回HCID 31297Methanesulfonyl chlorideHCID 67958303Methyl 5-chloro-2-(3-hydroxyazetidin-1-yl)nicotinate

生成物 1

HCID 86697874Methyl 5-chloro-2-(3-((methylsulfonyl)oxy)azetidin-1-yl)nicotinate収率 674.1%

反応条件

温度
0 °C

実験手順

To an ice cooled stirred solution of methyl 5-chloro-2-(3-hydroxyazetidin-1-yl)nicotinate (D62) (66 g, 0.27 mol) and triethylamine (56.86 ml, 0.40 mol) in dimethylformamide (500 ml) methanesulfonylchloride (23.15 ml, 0.29 mol) was added dropwise maintaining the temperature at 0° C. The reaction mixture was stirred at 0° C. for 3.5 h then methanesulfonyl chloride (6.3 ml, 0.037 mol) and triethylamine (18.9 ml, 0.135 mol) were added and the reaction mixture was stirred for 3 h at 0° C. After this time the formed solid was filtered off. Water (700 ml) was added to the filtrate. The formed solid was filtered off, washed with water (400 ml) and dried under vacuo to afford the title compound (D63) (80 g).

後処理

  1. additionwas added dropwise
  2. stirringthe reaction mixture was stirred for 3 h at 0° C
  3. filtrationAfter this time the formed solid was filtered off
  4. additionWater (700 ml) was added to the filtrate
  5. filtrationThe formed solid was filtered off
  6. washwashed with water (400 ml)
  7. customdried under vacuo

出典と根拠

ORDレコード
ord-7a1a31ba7c184be0a9d3b2cfd6a2e82a
出典データセット
uspto-grants-2014_09
特許番号
US08828987B2

関連ノート

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