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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
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HRID 899151 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 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 ester수율 102.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4c082f8c0ba5468e85ea4840b3555b6c
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07354917B2

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