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Potassium Iodide → 3-(2-Methoxy-5-methylphenyl)-3-phenyl propanoic acid-(3-benzyl-3-azabicyclo[3.1.0]hexane-6-yl-carbamoyl)methyl ester

HRID 2110548
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HRID 2110548 반응식
C(N1CC2C(C2[CH:14](Cl)[C:15](N)=[O:16])C1)C1C=CC=CC=1.[CH2:19]([N:26]1[CH2:31][CH:30]2[CH:28]([CH:29]2[NH2:32])[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.ClC[C:35](Cl)=[O:36].[I-].[K+].COC1C=CC(C)=CC=1[CH:49]([CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:50]([OH:52])=[O:51].N12CCCN=C1CCCCC2.[C:71]1(C)[C:72]([CH3:77])=[CH:73][CH:74]=[CH:75][CH:76]=1>>[CH2:19]([N:26]1[CH2:31][CH:30]2[CH:28]([CH:29]2[NH:32][C:15]([CH2:14][O:52][C:50](=[O:51])[CH2:49][CH:53]([C:76]2[CH:71]=[C:72]([CH3:77])[CH:73]=[CH:74][C:75]=2[O:36][CH3:35])[C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)=[O:16])[CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 7

HCID 4875Potassium IodideHCID 6577Chloroacetyl chlorideHCID 7237O-XyleneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 185069973-Benzyl-3-azabicyclo(3.1.0)hexan-6-amine2회HCID 68868912(2-Methoxy-5-methylphenyl)-3-phenyl propanoic acid
HCID 68872315
3-Benzyl-3-azabicylo[3.1.0]hex-6-yl-2-chloroacetamide

생성물 1

HCID 688723053-(2-Methoxy-5-methylphenyl)-3-phenyl propanoic acid-(3-benzyl-3-azabicyclo[3.1.0]hexane-6-yl-carbamoyl)methyl ester

실험 절차

The compound, 3-benzyl-3-azabicylo[3.1.0]hex-6-yl-2-chloroacetamide, 150 mg, 0.65 mmole, 1 eq (prepared by reacting 3-benzyl-3-azabicylo[3.1.0]hex-6-yl amine with 2-chloroacetyl chloride. The compound 3-benzyl-3-azabicyclo[3.1.0]hex-6-ylamine, in turn, can be prepared following the procedure of T. F. Braish et al., Synlett 1996, 1100) was dissolved in xylene. To the reaction mixture, potassium iodide was added with subsequent addition of (2-methoxy-5-methylphenyl)-3-phenyl propanoic acid (230 mg, 0.85 mmole, 1.5 eq) and 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction mixture was refluxed for 2 hours. Xylene was removed under pressure and the residue was dissolved in dichloromethane. The organic compound was then purified through column chromatography using 60% ethyl acetate in hexane.

후처리

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. customXylene was removed under pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. customThe organic compound was then purified through column chromatography

출처 및 근거

ORD 기록
ord-fc65d97cc0de434d9d4869b3c3e6cf6c
출처 데이터셋
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07517905B2

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