Diisopropylethylamine → benzyl 6-chloro-2-fluoro-3-(3-(4-methoxyphenoxy)-N-(3-(4-methoxyphenoxy)propylsulfonyl)propylsulfonamido)benzoate

HRID 1943949ノート

反応式

HRID 1943949 の反応式
[NH2:1][C:2]1[C:3]([F:19])=[C:4]([C:15]([Cl:18])=[CH:16][CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[CH3:20][O:21][C:22]1[CH:35]=[CH:34][C:25]([O:26][CH2:27][CH2:28][CH2:29][S:30](Cl)(=[O:32])=[O:31])=[CH:24][CH:23]=1.C(N([CH:42]([CH3:44])[CH3:43])C(C)C)C>C(Cl)Cl>[Cl:18][C:15]1[C:4]([C:5]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:6])=[C:3]([F:19])[C:2]([N:1]([S:30]([CH2:29][CH2:28][CH2:27][O:26][C:43]2[CH:42]=[CH:44][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)(=[O:32])=[O:31])[S:30]([CH2:29][CH2:28][CH2:27][O:26][C:25]2[CH:34]=[CH:35][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)(=[O:32])=[O:31])=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 51420933-(4-Methoxyphenoxy)propane-1-sulfonyl chlorideHCID 58087305Benzyl 3-amino-6-chloro-2-fluorobenzoate

生成物 1

HCID 131730287benzyl 6-chloro-2-fluoro-3-(3-(4-methoxyphenoxy)-N-(3-(4-methoxyphenoxy)propylsulfonyl)propylsulfonamido)benzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

A 100 mL, round-bottomed flask was charged with benzyl 3-amino-6-chloro-2-fluorobenzoate (1.0 g, 3.58 mmol), 3-(4-methoxyphenoxy)propane-1-sulfonyl chloride (2.84 g, 10.7 mmol), N-ethyl-N-isopropylpropan-2-amine (1.91 mL, 10.7 mmol) and DCM (15 mL). The reaction mixture was stirred at −78° C. until LC-MS showed that the starting material had been consumed (about 12 hours). Then the reaction mixture was cooled to room temperature and partitioned between EtOAc (500 mL) and water (200 mL). The phases were separated, and the aqueous phase was extracted with EtOAc (3×200 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield crude benzyl 6-chloro-2-fluoro-3-(3-(4-methoxyphenoxy)-N-(3-(4-methoxyphenoxy)propylsulfonyl)propylsulfonamido)benzoate. The crude product was used in the next step.

後処理

  1. customhad been consumed (about 12 hours)
  2. temperatureThen the reaction mixture was cooled to room temperature
  3. custompartitioned between EtOAc (500 mL) and water (200 mL)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with EtOAc (3×200 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-f2dde63bae6f46b197ac9d77977941e6
出典データセット
uspto-grants-2013_03
特許番号
US08394795B2

反応ノート

読み込み中…