Water → (R)-N-[4-(4-Bromophenylsulphonyl)-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 841182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 841182
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].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[C:29]([Cl:34])[CH:28]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1.O>ClCCl.CN(C=O)C>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([C:27]2[CH:33]=[CH:32][C:30]([NH:31][C:9](=[O:10])[C@:8]([OH:7])([CH3:16])[C:12]([F:15])([F:14])[F:13])=[C:29]([Cl:34])[CH:28]=2)(=[O:26])=[O:25])=[CH:22][CH:23]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 65578Oxalyl chlorideHCID 2760712(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acidHCID 226212634-(4-Bromophenylsulphonyl)-2-chloroaniline

Produkt 1

HCID 69113232(R)-N-[4-(4-Bromophenylsulphonyl)-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamideAusbeute 33,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Oxalyl chloride (0.029 ml) was added to a stirred suspension of (R)-(+)-2-hydroxy-2-methyl-3,3,3-trifluoropropanoic acid (Method 9) (0.047 g) in dichloromethane (3 ml) containing DMF (1 drop). The mixture was stirred at ambient temperature for 30 minutes and was then added to a solution of 4-(4-bromophenylsulphonyl)-2-chloroaniline (Method 12) (0.104 g) in dichloromethane (3 ml) and stirred a further 1 hour. Water (10 ml) was added and the mixture was extracted with dichloromethane (3×20 ml). The organic extracts were combined, washed with brine then dried. Volatile material was removed by evaporation and the residue was purified by flash chromatography on silica gel eluting with 1% methanol/dichloromethane to give the title compound (0.049 g) as a foam. NMR (CDCl3): 1.78 (s, 3H), 7.65 (d, 2H), 7.8 (m, 3H), 8.0 (s, 1H), 8.6 (d, 2H), 9.3 (s, 1H);MS: 485 (M+).

Aufarbeitung

  1. stirringstirred a further 1 hour
  2. extractionthe mixture was extracted with dichloromethane (3×20 ml)
  3. washwashed with brine
  4. customthen dried
  5. customVolatile material was removed by evaporation
  6. customthe residue was purified by flash chromatography on silica gel eluting with 1% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-12bdfd3f34214fa6aeb8cb3e7022f58b
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06369273B1

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