rel-(3R,5S)-3,5-Dimethylpiperidine → 2,3-Dichloro-5-(cis-3,5-dimethylpiperidinosulfonyl)benzoic Acid

HRID 1730601ノート

反応式

HRID 1730601 の反応式
[CH3:1][C@H:2]1[CH2:7][C@@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.[Cl:9][C:10]1[C:18]([Cl:19])=[CH:17][C:16]([S:20](Cl)(=[O:22])=[O:21])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>C(Cl)Cl>[Cl:9][C:10]1[C:18]([Cl:19])=[CH:17][C:16]([S:20]([N:4]2[CH2:5][C@H:6]([CH3:8])[CH2:7][C@H:2]([CH3:1])[CH2:3]2)(=[O:22])=[O:21])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

参加物

4

反応物 2

HCID 641101rel-(3R,5S)-3,5-DimethylpiperidineHCID 205061302,3-Dichloro-5-(chlorosulfonyl)benzoic acid

生成物 1

HCID 536984792,3-Dichloro-5-(cis-3,5-dimethylpiperidinosulfonyl)benzoic Acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To cis-3,5-dimethylpiperidine (374 mg.; 3.3 m moles) in 3 ml. of methylene chloride is added 192 mg. (0.66 m moles) of 2,3-dichloro-5-chlorosulfonylbenzoic acid and the mixture heated to refluxfor 1.5 hrs. The solvent is removed under reduced pressure, and the residueis partitioned between 25 ml. of 1N sodium hydroxide solution and diethyl ether. The aqueous layer is separated, acidified with 6N hydrochloric acidand the resulting precipitated product filtered and dried, 230 mg., m.p. 235°-238° C. Recrystallization from acetonitrile gave the purified product, m.p. 244°-245° C.

後処理

  1. customThe solvent is removed under reduced pressure
  2. customthe residueis partitioned between 25 ml
  3. customThe aqueous layer is separated
  4. customthe resulting precipitated product
  5. filtrationfiltered
  6. customdried
  7. customRecrystallization from acetonitrile
  8. customgave the purified product, m.p. 244°-245° C.

出典と根拠

ORDレコード
ord-ad060d491d7f4f7ca74db3fe6d62c2e2
出典データセット
uspto-grants-1976_11
特許番号
US03992441

反応ノート

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