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

HRID 355138노트

반응식

HRID 355138 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 reflux for 1.5 hrs. The solvent is removed under reduced pressure, and the residue is partitioned between 25 ml. of 1 N sodium hydroxide solution and diethyl ether. The aqueous layer is separated, acidified with 6 N hydrochloric acid and 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. temperatureto reflux for 1.5 hrs
  2. customThe solvent is removed under reduced pressure
  3. customthe residue is partitioned between 25 ml
  4. customThe aqueous layer is separated
  5. customthe resulting precipitated product
  6. filtrationfiltered
  7. customdried
  8. customRecrystallization from acetonitrile
  9. customgave the purified product, m.p. 244°-245° C.

출처 및 근거

ORD 기록
ord-282f007caae047a3a7fe83f18051cea4
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04377521

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