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 2110548Notes

Reaction equation

HRID 2110548 reaction equation
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

Participants

8

Reactant 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×HCID 68868912(2-Methoxy-5-methylphenyl)-3-phenyl propanoic acidHCID 688723153-Benzyl-3-azabicylo[3.1.0]hex-6-yl-2-chloroacetamide

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fc65d97cc0de434d9d4869b3c3e6cf6c
Source dataset
uspto-grants-2009_04
Patent number
US07517905B2

Reaction notes

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