(R)-(+)-3-Chlorostyrene oxide → HCID 54219870, compound

HRID 1069089Notes

Reaction equation

HRID 1069089 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][NH2:20])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C@H:25]1[O:27][CH2:26]1>[N+](C)([O-])=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][NH:20][CH2:26][C@@H:25]([C:24]3[CH:28]=[CH:29][CH:30]=[C:22]([Cl:21])[CH:23]=3)[OH:27])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 21191156HCID 21191156, compound

Product 1

HCID 54219870HCID 54219870, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A solution of methyl-3′-[(2-amino)ethoxy]-[1,1′-biphenyl]-3-carboxylate (284.5 mg) and (R)-(-)-3-chlorostyrene oxide (124 mg) in nitromethane (4.0 mL) was heated at 70-75° C. for 20 h. The mixture was concentrated with a rotary evaporator to afford the crude product. Purification by silica gel chromatography (eluting with ethyl acetate followed by 10:1 ethyl acetate: methanol followed by 3:1 ethyl acetate: methanol) afforded the title compound (190.6 mg) as a colorless oil.

Workup

  1. concentrationThe mixture was concentrated with a rotary evaporator
  2. customto afford the crude product
  3. customPurification
  4. washby silica gel chromatography (eluting with ethyl acetate followed by 10:1 ethyl acetate: methanol followed by 3:1 ethyl acetate: methanol)

Sources & evidence

ORD record
ord-f8291a36ade346daa5a24d7bfe88fcd0
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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