Acetic Acid → [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2-chloroanilino)methyl]benzoate

HRID 1497991ノート

反応式

HRID 1497991 の反応式
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:32])[CH:5]=[C:6]([Cl:31])[C:7]=1[CH2:8][C@H:9]([O:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=O)[CH:23]=1)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.[Cl:33][C:34]1[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=1[NH2:36].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:32])[CH:5]=[C:6]([Cl:31])[C:7]=1[CH2:8][C@H:9]([O:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:36][C:35]2[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=2[Cl:33])[CH:23]=1)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 72402-ChloroanilineHCID 5049666Sodium triacetoxyborohydrideHCID 86720715[(1S)-2-(3,5-Dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-formylbenzoate

生成物 1

HCID 86720716[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2-chloroanilino)methyl]benzoate収率 67%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-formylbenzoate (332 mg, 0.697 mmol) and 2-chloroaniline (0.077 mL, 0.732 mmol) in anhydrous DCM (3.5 mL) was added acetic acid (0.042 mL, 0.732 mmol). The mixture was stirred at room temperature for 24 hours. NaBH(OAc)3 (369 mg, 1.74 mmol) was added, and the mixture was stirred at room temperature for 24 hours. After addition of water (2.5 mL), the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered through a phase separator, and the solvent was removed in vacuo. The crude material was purified by silica gel column chromatography eluting with 1:1 DCM:EtOAc to afford the title compound as a white solid (274 mg, 67%).

後処理

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. filtrationThe reaction mixture was filtered through a phase separator
  4. customthe solvent was removed in vacuo
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluting with 1:1 DCM

出典と根拠

ORDレコード
ord-f7561fab2d70403ebe1c58bab269d97b
出典データセット
uspto-grants-2015_12
特許番号
US09199980B2

反応ノート

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