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

HRID 2110549Notes

Reaction equation

HRID 2110549 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.[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][C:35]=1[CH:41]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH2:42][C:43]([OH:45])=[O:44].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:44][C:43](=[O:45])[CH2:42][CH:41]([C:35]2[CH:36]=[C:37]([CH3:40])[CH:38]=[CH:39][C:34]=2[O:33][CH3:32])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=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 34683223-(2-Methoxy-5-methylphenyl)-3-phenylpropanoic acidHCID 688740383-Benzyl-3-azabicyclo[3.1.0]hex-6-yl-(4-bromobutyl)-carbamic acid t-butyl ester

Product 1

HCID 688700323-(2-Methoxy-5-methylphenyl)-3-phenyl propionic acid 4-[(3-benzyl-3-azabicyclo[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 the reaction mixture, 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid (203 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 compound, 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid 4-[(3-benzyl-3-azabicyclo[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-771cda2b2e1941af854f6f7f1d460d06
Source dataset
uspto-grants-2009_04
Patent number
US07517905B2

Reaction notes

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