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 1529540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1529540
C(O)(C(F)(F)F)=O.C([O:15][C:16]1[C:50]([CH:51]=[O:52])=[CH:49][CH:48]=[CH:47][C:17]=1[C:18]([O:20][C@H:21]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH:39]([F:41])[F:40])=[C:34]([O:42][CH2:43][CH:44]2[CH2:46][CH2:45]2)[CH:33]=1)[CH2:22][C:23]1[C:28]([Cl:29])=[CH:27][N+:26]([O-:30])=[CH:25][C:24]=1[Cl:31])=[O:19])C1C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:51]([C:50]1[C:16]([OH:15])=[C:17]([CH:47]=[CH:48][CH:49]=1)[C:18]([O:20][C@H:21]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH:39]([F:40])[F:41])=[C:34]([O:42][CH2:43][CH:44]2[CH2:46][CH2:45]2)[CH:33]=1)[CH2:22][C:23]1[C:24]([Cl:31])=[CH:25][N+:26]([O-:30])=[CH:27][C:28]=1[Cl:29])=[O:19])=[O:52]

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 fit 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 fit
  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-5b7fca5398344aeb836893a048e26b0e
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090606B2

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