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

HRID 1730601노트

반응식

HRID 1730601 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-ad060d491d7f4f7ca74db3fe6d62c2e2
출처 데이터셋
uspto-grants-1976_11
특허 번호
US03992441

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