(+)-Styrene oxide → methyl 4'-[2-[benzyl[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(isopropylamino)-4-biphenylcarboxylate

HRID 2220378Notes

Reaction equation

HRID 2220378 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([NH:27][CH:28]([CH3:30])[CH3:29])[CH:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]1[O:39][C@@H:32]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(O)C>[CH2:1]([N:8]([CH2:31][C@H:32]([OH:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([NH:27][CH:28]([CH3:30])[CH3:29])[CH:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 114705(+)-Styrene oxideHCID 69103631Methyl 4'-[2-(benzylamino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylate

Product 1

HCID 69103734methyl 4'-[2-[benzyl[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(isopropylamino)-4-biphenylcarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4′-[2-(benzylamino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylate (250 mg) in ethanol (15 ml) was added (R)-(+)-styreneoxide (142 μl) at room temperature, and the mixture was stirred under reflux for 48 hours. The mixture was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to give methyl 4′-[2-[benzyl[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(isopropylamino)-4-biphenylcarboxylate (251 mg).

Workup

  1. temperatureunder reflux for 48 hours
  2. customThe mixture was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-8781383c3f4643a6adfc9e8ea92acf1e
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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