二甲基对苯二胺二盐酸 → 2-[2-(4-Fluorophenyl)acetyl]4-methylene-pyrazolidine-1-carboxylic acid benzyl ester

HRID 22668

反应方程式

HRID 22668 反应方程式
[OH-].[Na+].[CH2:3]([O:10][C:11]([N:13]1[CH2:17][C:16](=[CH2:18])[CH2:15][NH:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=[O:28])=[CH:22][CH:21]=1>O.C(Cl)Cl.O>[CH2:3]([O:10][C:11]([N:13]1[CH2:17][C:16](=[CH2:18])[CH2:15][N:14]1[C:27](=[O:28])[CH2:26][C:23]1[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参与物

6

反应物 3

HCID 14798二甲基对苯二胺二盐酸HCID 3744988对氟苯乙酰氯HCID 12970153Benzyl 4-methylidenepyrazolidine-1-carboxylate

产物 1

HCID 129701542-[2-(4-Fluorophenyl)acetyl]4-methylene-pyrazolidine-1-carboxylic acid benzyl ester收率 62%

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 21908982Water methylene chloride溶剂

实验过程

Sodium hydroxide (0.12 g, 3 mmol) is dissolved in a 1:2 water/methylene chloride solution (30 mL) with rapid stirring followed by the addition of 4-methylene-pyrazolidine-1-carboxylic acid 1-benzyl ester, 9, (0.62 g, 2.8 mmol) at room temperature. (4-Fluorophenyl)acetyl chloride (0.39 mL, 4.2 mmol) is added and the reaction is allowed to stir for 18 hours after which time the reaction mixture is diluted with water (10 mL) and the layers allowed to separate. The aqueous layer is extracted with methylene chloride, the organic layers combined, dried, and filtered. Concentration in vacuo affords the crude product which is purified over silica (1:3 ethyl acetate/hexane) to provide 0.54 g (62% yield) of the desired product.

后处理

  1. stirringto stir for 18 hours after which time the reaction mixture
  2. customto separate
  3. extractionThe aqueous layer is extracted with methylene chloride
  4. customdried
  5. filtrationfiltered
  6. concentrationConcentration in vacuo
  7. customaffords the crude product which
  8. customis purified over silica (1:3 ethyl acetate/hexane)

来源与证据

ORD记录
ord-81e393028ae24d67914a3f1a874c6abd
来源数据集
uspto-grants-2005_02
专利号
US06849627B2

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