Sodium Hydroxide → 2-[2-(4-Fluorophenyl)acetyl]4-methylene-pyrazolidine-1-carboxylic acid benzyl ester

HRID 413034

反応式

HRID 413034 の反応式
[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

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 37449884-Fluorophenylacetyl chlorideHCID 12970153Benzyl 4-methylidenepyrazolidine-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21908982Water methylene chloride溶媒

実験手順

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, 2, (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.

後処理

  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)

出典と根拠

ORDレコード
ord-5ab1801024234f48a4a91e88e5bfe9da
出典データセット
uspto-grants-2003_05
特許番号
US06566357B1

関連ノート

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