Potassium Carbonate → 7-[2-(4-Cyanobenzenesulfonylamino)ethyl]-9-oxa-3,7-diazabicyclo-[3.3.1]nonane-3-carboxylic acid tert-butyl ester

HRID 1992344ノート

反応式

HRID 1992344 の反応式
Br[CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[C:16]([O:20][C:21]([N:23]1[CH2:30][CH:29]2[O:31][CH:25]([CH2:26][NH:27][CH2:28]2)[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:16]([O:20][C:21]([N:23]1[CH2:24][CH:25]2[O:31][CH:29]([CH2:28][N:27]([CH2:2][CH2:3][NH:4][S:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=3)(=[O:7])=[O:6])[CH2:26]2)[CH2:30]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonaneHCID 43133684N-(2-bromoethyl)-4-cyanobenzenesulfonamide

生成物 1

HCID 685209557-[2-(4-Cyanobenzenesulfonylamino)ethyl]-9-oxa-3,7-diazabicyclo-[3.3.1]nonane-3-carboxylic acid tert-butyl ester収率 67.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

A suspension of N-(2-bromoethyl)-4-cyanobenzenesulfonamide (5 g, 0.017 mol; see step (i) above), 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (3.96 g, 0.0173 mol; see WO 01/28992) and potassium carbonate (3.6 g, 0.025 mol) in acetonitrile (50 mL) was stirred at 60° C. overnight. The reaction mixture was filtered and the solvent concentrated under reduced pressure to yield the crude product, which was purified by column chromatography (using methanol in chloroform as the eluent) to yield (5 g) of the sub-title compound as pale yellow solid.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe solvent concentrated under reduced pressure
  3. customto yield the crude product, which
  4. customwas purified by column chromatography (

出典と根拠

ORDレコード
ord-1922c865ab9649e2aa5618061451df08
出典データセット
uspto-grants-2010_01
特許番号
US07648985B2

反応ノート

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