1,4-Dioxane → t-Butyl 3-[[5-chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridin-2-yl]amino]propionate

HRID 2080447ノート

反応式

HRID 2080447 の反応式
Cl.[C:2]([O:6][C:7](=[O:11])[CH2:8][CH2:9][NH2:10])([CH3:5])([CH3:4])[CH3:3].O1CCOCC1.Cl[C:19]1[CH:24]=[C:23]([CH:25]([S:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])[C:22]([Cl:42])=[CH:21][N:20]=1>C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>[Cl:42][C:22]1[C:23]([CH:25]([S:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])=[CH:24][C:19]([NH:10][CH2:9][CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:11])=[N:20][CH:21]=1

参加物

6

反応物 3

HCID 312751,4-DioxaneHCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 231145672,5-Dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine

生成物 1

HCID 23114708t-Butyl 3-[[5-chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridin-2-yl]amino]propionate収率 20.9%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 11430Potassium Carbonate溶媒

実験手順

In a small amount of a saturated aqueous solution of potassium carbonate was dissolved β-alanine t-butyl ester hydrochloride (1.5 g), followed by extraction with methylene chloride. The extract was dried and concentrated into 720 mg of β-alanine t-butyl ester in the free form. The resulting ester and a 1,4-dioxane (2.0 ml) solution of the 2,5-dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine (300 mg, 0.72 mmol) obtained in Example 54 was stirred at 120° C. for 4 days under an argon atmosphere. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate. The diluted mixture was washed with water and brine, dried and then concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to give the title compound (79 mg, 16%) as an oil.

後処理

  1. extractionfollowed by extraction with methylene chloride
  2. customThe extract was dried
  3. concentrationconcentrated into 720 mg of β-alanine t-butyl ester in the free form
  4. washThe diluted mixture was washed with water and brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel chromatography (hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-2d2d59f7a84b4546903d80a791ddec2c
出典データセット
uspto-grants-2011_04
特許番号
US07932271B2

反応ノート

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