1-Bromo-3-chloropropane → 3-(2-Benzyloxy-5-methylphenyl)-3-phenyl propionic acid 4-[(3-benzyl-3-azabicylo[3.1.0]hex-6-yl)-ethoxy carbonylamino]butyl ester

HRID 2110550Notes

Reaction equation

HRID 2110550 reaction equation
[C:1]([O:5][C:6](=[O:26])[N:7]([CH:13]1[CH:18]2[CH:14]1[CH2:15][N:16]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:17]2)[CH2:8][CH2:9][CH2:10][CH2:11]Br)(C)(C)[CH3:2].BrCCCCl.[CH2:32]([O:39][C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][C:41]=1[CH:47]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:48][C:49]([OH:51])=[O:50])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.N12CCCN=C1CCCCC2>C1(C)C(C)=CC=CC=1>[CH2:19]([N:16]1[CH2:15][CH:14]2[CH:18]([CH:13]2[N:7]([C:6]([O:5][CH2:1][CH3:2])=[O:26])[CH2:8][CH2:9][CH2:10][CH2:11][O:50][C:49](=[O:51])[CH2:48][CH:47]([C:41]2[CH:42]=[C:43]([CH3:46])[CH:44]=[CH:45][C:40]=2[O:39][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH2:17]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 672392883-(2-Benzyloxy-5-methylphenyl) 3-phenyl propionic acidHCID 688740383-Benzyl-3-azabicyclo[3.1.0]hex-6-yl-(4-bromobutyl)-carbamic acid t-butyl ester

Product 1

HCID 688737293-(2-Benzyloxy-5-methylphenyl)-3-phenyl propionic acid 4-[(3-benzyl-3-azabicylo[3.1.0]hex-6-yl)-ethoxy carbonylamino]butyl ester

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The compound, 3-benzyl-3-azabicyclo[3.1.0]hex-6-yl-(4-bromobutyl)-carbamic acid t-butyl ester, 211.5 mg, 0.5 mmole, 1 eq (prepared by reacting boc-protected 3-benzyl-3-azabicylo[3.1.0]hex-6-yl amine, which in turn, was prepared following the procedure of T. F. Braish et al., Synlett, 1996, 1100, with 1-bromo-3-chloropropane) was dissolved in xylene (15 ml). To this reaction mixture, 3-(2-benzyloxy-5-methylphenyl) 3-phenyl propionic acid (260 mg, 0.75 mmole, 1.5 eq) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.75 mmole, 1.5 eq) were added. The resulting reaction mixture was refluxed for 2 hrs. Xylene was removed under reduced pressure and the residue was purified by column chromatography by using ethyl acetate in hexane solvent system to yield the organic compound, 3-(2-benzyloxy-5-methylphenyl)-3-phenyl propionic acid 4-[(3-benzyl-3-azabicylo[3.1.0]hex-6-yl)-ethoxy carbonylamino]butyl ester.

Workup

  1. customwas prepared
  2. customThe resulting reaction mixture
  3. temperaturewas refluxed for 2 hrs
  4. customXylene was removed under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f2ce9de509324d5e9ba425d5acdba760
Source dataset
uspto-grants-2009_04
Patent number
US07517905B2

Reaction notes

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