(R)-5-(Oxiran-2-ylmethoxy)quinoline → 3-{4-[2-(R)-Hydroxy-3-(quinolin-5-yloxy)-propyl]-piperazin-1-yl}-3-oxopropionic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

HRID 2120888Notes

Reaction equation

HRID 2120888 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21](=[O:31])[CH2:22][C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:32]1[CH2:34][C@@H:33]1[CH2:35][O:36][C:37]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:38]=1[CH:39]=[CH:40][CH:41]=[N:42]2>C(O)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21](=[O:31])[CH2:22][C:23]([N:25]2[CH2:30][CH2:29][N:28]([CH2:34][C@@H:33]([OH:32])[CH2:35][O:36][C:37]3[CH:46]=[CH:45][CH:44]=[C:43]4[C:38]=3[CH:39]=[CH:40][CH:41]=[N:42]4)[CH2:27][CH2:26]2)=[O:24])[CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 11735808(R)-5-(Oxiran-2-ylmethoxy)quinolineHCID 129924703-(Piperazin-1-yl)-3-oxopropionic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

Product 1

HCID 129924713-{4-[2-(R)-Hydroxy-3-(quinolin-5-yloxy)-propyl]-piperazin-1-yl}-3-oxopropionic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(Piperazin-1-yl)-3-oxopropionic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (38) (209.5 mg; 0.497 mmol) is dissolved in ethanol (12 mL) at ambient temperature. (R)-5-Oxiranylmethoxy-quinoline (2) (100.0 mg; 0.497 mmol) is added, then the mixture is refluxed for 15 hours. After cooling to ambient temperature, the solution is concentrated in vacuo at 40° C. The residue is purified via silica gel chromatography with gradient elution (neat ethyl acetate, then 50%→100% acetone in hexanes, then 5% ethanol in acetone) affording the desired product as a solid. ESMS: MH− 623.4

Workup

  1. temperaturethe mixture is refluxed for 15 hours
  2. concentrationthe solution is concentrated in vacuo at 40° C
  3. customThe residue is purified via silica gel chromatography with gradient elution (neat ethyl acetate

Sources & evidence

ORD record
ord-c353f250e68e4b8ebe8e38935ea6aec5
Source dataset
uspto-grants-2004_02
Patent number
US06693099B2

Reaction notes

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