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

HRID 337218ノート

反応式

HRID 337218 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-23c5ce2b9fbe4768b6193d9812187517
出典データセット
uspto-grants-2014_11
特許番号
US08889716B2

反応ノート

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