Trifluoroacetic acid → [(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-formyl-2-hydroxy-benzoate

HRID 1497995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497995
C(O)(C(F)(F)F)=O.[CH:8]1([CH2:11][O:12][C:13]2[CH:14]=[C:15]([C@@H:23]([O:34][C:35](=[O:52])[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([CH:42]=[O:43])[C:37]=3[O:44]CC3C=CC=CC=3)[CH2:24][C:25]3[C:30]([Cl:31])=[CH:29][N+:28]([O-:32])=[CH:27][C:26]=3[Cl:33])[CH:16]=[CH:17][C:18]=2[O:19][CH:20]([F:22])[F:21])[CH2:10][CH2:9]1>C1(C)C=CC=CC=1.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:8]1([CH2:11][O:12][C:13]2[CH:14]=[C:15]([C@@H:23]([O:34][C:35](=[O:52])[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([CH:42]=[O:43])[C:37]=3[OH:44])[CH2:24][C:25]3[C:30]([Cl:31])=[CH:29][N+:28]([O-:32])=[CH:27][C:26]=3[Cl:33])[CH:16]=[CH:17][C:18]=2[O:19][CH:20]([F:21])[F:22])[CH2:10][CH2:9]1

Komponenten

6

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86720698[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl] 2-benzyloxy-3-formyl-benzoate

Produkt 1

HCID 86720699[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-formyl-2-hydroxy-benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

TFA (0.4 mL) was carefully added to a solution of [(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]2-benzyloxy-3-formyl-benzoate (116 mg, 0.18 mmol) in toluene (0.8 mL) at 0° C. The resulting mixture was stirred at 0° C. for 50 minutes. The solution was diluted with DCM (20 mL) and sat. NaHCO3 (20 mL). The layers were separated over a hydrophobit frit and the organic phase concentrated in vacuo, the residue azeotroped with toluene to dryness. The yellow gum (120 mg) was used in the next step without further purification.

Aufarbeitung

  1. customThe layers were separated over a hydrophobit frit
  2. concentrationthe organic phase concentrated in vacuo
  3. customthe residue azeotroped with toluene to dryness
  4. customThe yellow gum (120 mg) was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-8d106443b25446c3a51954e4cf83e1b1
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199980B2

Notizen zur Reaktion

Wird geladen…