Hydroxylamine → (2S)-3-[4-(3-{4-[(4-Fluoro-phenyl)-hydroxyimino-methyl]-phenoxy}-prop-1-ynyl)-phenyl]-2-methoxy-propionic acid

HRID 459090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459090
[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([C:8]2[CH:30]=[CH:29][C:11]([O:12][CH2:13][C:14]#[C:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C@H:23]([O:27][CH3:28])[C:24]([OH:26])=[O:25])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.[NH2:33][OH:34].N1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6](=[N:33][OH:34])[C:8]2[CH:30]=[CH:29][C:11]([O:12][CH2:13][C:14]#[C:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C@H:23]([O:27][CH3:28])[C:24]([OH:26])=[O:25])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 787HydroxylamineHCID 1049PyridineHCID 58822979(2S)-3-(4-{3-[4-(4-Fluoro-benzoyl)-phenoxy]-prop-1-ynyl}-phenyl)-2-methoxy-propionic acid

Produkt 1

HCID 86596242(2S)-3-[4-(3-{4-[(4-Fluoro-phenyl)-hydroxyimino-methyl]-phenoxy}-prop-1-ynyl)-phenyl]-2-methoxy-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

(2S)-3-(4-{3-[4-(4-Fluoro-benzoyl)-phenoxy]-prop-1-ynyl}-phenyl)-2-methoxy-propionic acid from Example 12 (0.01 mmol, 1 eq) was mixed with Hydroxylamine chlorydrate (4 eq), pyridine (10 eq) and Ethanol (2 ml) and the mixture reaction was stirred overnight. The ethanol was evaporated under vacuo and HCl 0.5% was added to the residue to pH=3. Extracted with Ethyl Acetate and concentrated to give the title product as a mixture of two oximes. MS(ES) for C26H22FNO5 [M+H]+: 448.2, [M−H]−: 446.2.

Aufarbeitung

  1. customthe mixture reaction
  2. customThe ethanol was evaporated under vacuo and HCl 0.5%
  3. additionwas added to the residue to pH=3
  4. extractionExtracted with Ethyl Acetate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7b6f84c7b726439a9faff63dbb8e8d61
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192982B2

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