Oxalyl chloride → (R)-N-(2,3-Dichloro-4-ethylsulphanylphenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 2120353

Reaktionsgleichung

Reaktionsgleichung von HRID 2120353
C(Cl)(=O)C(Cl)=O.[OH:7][C@@:8]([CH3:16])([C:12]([F:15])([F:14])[F:13])[C:9](O)=[O:10].[CH2:17]([S:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[C:22]([Cl:27])[C:21]=1[Cl:28])[CH3:18].C1(C2C=CC=C(C3C=CC=CC=3)N=2)C=CC=CC=1>C(Cl)Cl.CN(C=O)C>[Cl:27][C:22]1[C:21]([Cl:28])=[C:20]([S:19][CH2:17][CH3:18])[CH:26]=[CH:25][C:23]=1[NH:24][C:9](=[O:10])[C@:8]([OH:7])([CH3:16])[C:12]([F:15])([F:14])[F:13]

Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 729202,6-DiphenylpyridineHCID 2760712(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acidHCID 111836394-Ethylsulphanyl-2,3-dichloroaniline

Produkt 1

HCID 11268444(R)-N-(2,3-Dichloro-4-ethylsulphanylphenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamideAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Oxalyl chloride (0.75 ml) was added to a stirred suspension of (R)-(+)-2-hydroxy-2-methyl-3,3,3-trifluoropropanoic acid (Method 25) (1.37 g) in DCM (10 ml) containing DMF (1 drop). The mixture was stirred at ambient temperature for 18 hours and was then added to a solution of 4-ethylsulphanyl-2,3-dichloroaniline (Method 7) (1.92 g) and 2,6-diphenylpyridine (2.0 g) in DCM (50 ml). The mixture was stirred for 3 hours at room temperature, volatile material was removed by evaporation and the residue was purified by chromatography eluting with 0-20% EtOAc/isohexane to give the title compound (2.12 g) as a solid. NMR (CDCl3) 1.35 (t, 3H), 1.76 (s, 3H), 2.97 (q, 2H), 3.61 (s, 1H), 7.22 (d, 1H), 8.27 (d, 1H), 8.91 (s, 1H); m/z: 360.

Aufarbeitung

  1. stirringThe mixture was stirred for 3 hours at room temperature
  2. customvolatile material was removed by evaporation
  3. customthe residue was purified by chromatography
  4. washeluting with 0-20% EtOAc/isohexane

Quellen und Nachweise

ORD-Eintrag
ord-743b6c8217124af89c2f08a782b191e2
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06689909B1

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