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Acetic Acid → 7-(2-{1-[2-(4-Cyanophenoxy)ethyl]-3,3-dimethylureido}ethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

HRID 899151
ノート
印刷プレビュー

反応式

HRID 899151 の反応式
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][CH2:9][N:10]([CH2:16][CH:17]=O)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:5][CH:4]=1)#[N:2].[C:21]([O:25][C:26]([N:28]1[CH2:35][CH:34]2[O:36][CH:30]([CH2:31][NH:32][CH2:33]2)[CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(O)(=O)C.[BH3-]C#N.[Na+]>ClCCl.O>[C:21]([O:25][C:26]([N:28]1[CH2:29][CH:30]2[O:36][CH:34]([CH2:33][N:32]([CH2:17][CH2:16][N:10]([CH2:9][CH2:8][O:7][C:6]3[CH:19]=[CH:20][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:31]2)[CH2:35]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonaneHCID 860865631-[2-(4-Cyanophenoxy)ethyl]-3,3-dimethyl-1-(2-oxoethyl)urea

生成物 1

HCID 690786487-(2-{1-[2-(4-Cyanophenoxy)ethyl]-3,3-dimethylureido}ethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester収率 102.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

1-[2-(4-Cyanophenoxy)ethyl]-3,3-dimethyl-1-(2-oxoethyl)urea (4.5 g; see Preparation G above) was taken in dichloromethane (100 mL). 9-Oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (2.9 g, 0.013 mol; see WO 01/28992), followed by glacial acetic acid (1.47 g, 0.0245 mol), was added, and reaction mixture was stirred for 1 h. NaBH3CN (1.54 g, 0.024 mol) was added at 0° C., and stirring was continued overnight at room temperature. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with water and brine and then dried over sodium sulfate. Solvent evaporation, followed by purification by column chromatography, yielded the title compound (6.5 g).

後処理

  1. additionwas added
  2. customreaction mixture
  3. stirringstirring
  4. waitwas continued overnight at room temperature
  5. extractionextracted with dichloromethane
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customSolvent evaporation
  9. customfollowed by purification by column chromatography

出典と根拠

ORDレコード
ord-4c082f8c0ba5468e85ea4840b3555b6c
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07354917B2

反応ノート

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