phenylalaninol, (S)- → N-[(1S)-1-Benzyl-2-hydroxyethyl]-(2S)-2-[3-fluoro-4-(methylsulfonylamino)phenyl]propionamide

HRID 238925

Reaktionsgleichung

Reaktionsgleichung von HRID 238925
[F:1][C:2]1[CH:3]=[C:4]([CH:13]([C:15](CC)=[O:16])[CH3:14])[CH:5]=[CH:6][C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[NH2:19][C@H:20]([CH2:28][OH:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[CH2:21]([C@H:20]([NH:19][C:15](=[O:16])[C@H:13]([C:4]1[CH:5]=[CH:6][C:7]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])=[C:2]([F:1])[CH:3]=1)[CH3:14])[CH2:28][OH:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

4

Edukt 2

HCID 447213phenylalaninol, (S)-HCID 1317311832-[3-Fluoro-4-(metylsulfonylamino)phenyl]propion

Produkt 1

HCID 24754390N-[(1S)-1-Benzyl-2-hydroxyethyl]-(2S)-2-[3-fluoro-4-(methylsulfonylamino)phenyl]propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-[3-fluoro-4-(methylsulfonylamino)phenyl]propion acid (100 mg, 0.234 mmol) and L-phenyl alaninol (71 mg, 0.468 mmol) in CH2Cl2 (3 mL) was refluxed for 3 h and concentrated in vacuo. The residue was dissolved in MeOH (2 mL) and purified by flash column chromatography on silica gel using EtOAc:hexanes (2:1) to EtOAc:MeOH (20:1) as eluant to afford N-[(1S)-1-Benzyl-2-hydroxyethyl]-(2S)-2-[3-fluoro-4-(methylsulfonylamino)phenyl]propionamide.

Aufarbeitung

  1. temperaturewas refluxed for 3 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in MeOH (2 mL)
  4. custompurified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-09c0895840e8457380f08d0de98eabe0
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642657B2

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