Phenethylamine → [1-(3-Fluoro-4-phenethylcarbamoyl-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 337218노트

반응식

HRID 337218 반응식
S(Cl)(Cl)=O.[C:5]([O:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([S:19]([C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[C:24]([F:31])[CH:23]=2)(=[O:21])=[O:20])[CH2:15][CH2:14]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].N1C=CC=CC=1.[CH2:38]([NH2:46])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[C:5]([O:9][C:10](=[O:11])[NH:12][CH:13]1[CH2:14][CH2:15][N:16]([S:19]([C:22]2[CH:30]=[CH:29][C:25]([C:26](=[O:28])[NH:46][CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[C:24]([F:31])[CH:23]=2)(=[O:20])=[O:21])[CH2:17][CH2:18]1)([CH3:7])([CH3:8])[CH3:6]

참가 물질

6

반응물 4

HCID 1001PhenethylamineHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 710601234-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-2-fluoro-benzoic acid

생성물 1

HCID 71060106[1-(3-Fluoro-4-phenethylcarbamoyl-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester수율 100.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Thionyl chloride (0.16 g, 2.2 mmol) was added dropwise to a stirred solution of 4-(4-tert-butoxycarbonylamino-piperidine-1-sulfonyl)-2-fluoro-benzoic acid (0.3 g, 0.75 mmol) and pyridine (0.36 ml, 4.5 mmol) in DCM (10 ml). The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 4 hours, after this time phenethylamine (0.19 ml, 1.5 mmol) was added in one portion and stirring was continued for a further 12 hours. The mixture was then diluted with DCM (10 ml) before being washed sequentially with HCl (1M solution, 10 ml) and NaOH (1M solution, 10 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated to give the title compound (0.38 g, 74%) as a white foam which was taken on without further purification. Tr=2.16 min m/z (ES+) (M+Na+) 528.

후처리

  1. stirringstirring
  2. waitwas continued for a further 12 hours
  3. washbefore being washed sequentially with HCl (1M solution, 10 ml) and NaOH (1M solution, 10 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-23c5ce2b9fbe4768b6193d9812187517
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889716B2

반응 노트

불러오는 중…