Ethyl Acetate → HCID 22872206, compound

HRID 54519Notes

Reaction equation

HRID 54519 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N-:16][CH2:17][C@H:18](O)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CS(OS(C)(=O)=O)(=O)=O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>N1C=CC=CC=1.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[O:15][C@@H:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:17][N:16]=3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81560Methanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 178523399HCID 178523399, compound

Product 1

HCID 22872206HCID 22872206, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.24 g of 4'-chlorobiphenyl-4-carbonyl-[2(R)-hydroxy-2-phenylethyl]amide in 20 ml of pyridine is cooled in an ice bath and treated with a solution of 921 mg of methanesulfonic acid anhydride in dichloromethane. The reaction mixture is stirred for additional 16 hours at 5°, ethyl acetate and saturated aqueous sodium hydrogencarbonate are added, the organic layer is separated, dried and concentrated in vacuo. Vacuum flash chromatography on silica gel (toluene/ethyl acetate =3/1) yields the compound as pale yellow crystals; m.p.: 121.5° (recrystallized from ethanol); [α]D20 =+133.5° (c=1.3, methanol);

Workup

  1. customthe organic layer is separated
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a017c1503e254270bba7017fa1bbfd31
Source dataset
uspto-grants-1997_04
Patent number
US05622982

Reaction notes

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