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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
ノート
印刷プレビュー

反応式

HRID 2110548 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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-amine2 回HCID 68868912(2-Methoxy-5-methylphenyl)-3-phenyl propanoic acid
HCID 68872315
3-Benzyl-3-azabicylo[3.1.0]hex-6-yl-2-chloroacetamide

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fc65d97cc0de434d9d4869b3c3e6cf6c
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07517905B2

反応ノート

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