Phenacyl bromide → (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(vinyloxycarbonylamino)-acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1619517ノート

反応式

HRID 1619517 の反応式
[C:1]1([CH:7]([NH:19][C:20]([O:22][CH:23]=[CH2:24])=[O:21])[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:25][CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28]>CCOC(C)=O.C(#N)C>[Br-:25].[O:28]=[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:26][N+:13]12[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]1)[C@@H:11]([O:10][C:8](=[O:9])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[NH:19][C:20]([O:22][CH:23]=[CH2:24])=[O:21])[CH2:12]2

参加物

5

反応物 2

HCID 6259Phenacyl bromideHCID 67605833(R)-quinuclidin-3-yl 2-phenyl-2-(vinyloxycarbonylamino)acetate

生成物 1

HCID 86665828(3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(vinyloxycarbonylamino)-acetoxy)-1-azoniabicyclo[2.2.2]octane bromide収率 74.1%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(vinyloxycarbonylamino)acetate (C32) (70.0 mg, 0.21 mmol) in EtOAc (2 ml) and acetonitrile (0.5 ml), was added 2-bromo-1-phenylethanone (46.4 mg, 0.23 mmol). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The resulting solid was triturated with i-Pr2O/EtOAc (1/1) to obtain (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(vinyloxycarbonylamino)-acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (82.4 mg; 73% yield).

後処理

  1. customthe solvent was evaporated
  2. customThe resulting solid was triturated with i-Pr2O/EtOAc (1/1)

出典と根拠

ORDレコード
ord-46e44c7ad7fd43ce90534d00201d82ba
出典データセット
uspto-grants-2014_07
特許番号
US08772314B2

反応ノート

読み込み中…