Acetonitrile → (R)-3-(2-benzylamino-2-phenyl-acetoxy)-1-[2-(3-ethoxycarbonyl-isoxazol-5-yl)-2-oxo-ethyl]-1-azonia-bicyclo[2.2.2]octane bromide

HRID 1255074

反応式

HRID 1255074 の反応式
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:26])[CH:11]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2]2.C(#N)C.[Br:30][CH2:31][C:32]([C:34]1[O:38][N:37]=[C:36]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH:35]=1)=[O:33]>C(OCC)(=O)C>[Br-:30].[CH2:19]([NH:18][CH:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:10]([O:9][C@@H:3]1[CH:4]2[CH2:5][CH2:6][N+:1]([CH2:31][C:32]([C:34]3[O:38][N:37]=[C:36]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH:35]=3)=[O:33])([CH2:8][CH2:7]2)[CH2:2]1)=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 2736373Ethyl 5-(2-bromoacetyl)isoxazole-3-carboxylateHCID 46840418(R)-quinuclidin-3-yl 2-(benzylamino)-2-phenylacetate

生成物 1

HCID 86643228(R)-3-(2-benzylamino-2-phenyl-acetoxy)-1-[2-(3-ethoxycarbonyl-isoxazol-5-yl)-2-oxo-ethyl]-1-azonia-bicyclo[2.2.2]octane bromide収率 35.6%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Benzylamino-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (C80) (100 mg, 0.28 mmol) is dissolved in ethyl acetate (1.90 mL) and acetonitrile (0.95 mL) and ethyl 5-(2-bromoacetyl)isoxazole-3-carboxylate (82.0 mg, 0.31 mmol) is added. The orange solution is stirred at RT overnight. The suspension is evaporated and the crude is purified by flash chromatography (DCM/EtOH=93/7) to obtain the title compound as a pale brown solid (61 mg, 35% yield, bromide salt, mixture of diastereoisomers).

後処理

  1. customThe suspension is evaporated
  2. customthe crude is purified by flash chromatography (DCM/EtOH=93/7)

出典と根拠

ORDレコード
ord-f31eb4ab71344302a928cc83f4f83e72
出典データセット
uspto-grants-2013_06
特許番号
US08455646B2

関連ノート

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