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Triacetoxyperiodinane → N-[(5-fluoro-1-methyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester

HRID 2297067
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2297067
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([NH:14][C@H:15]([C:19]([NH:21][CH:22]([CH:31]([OH:44])[CH2:32][O:33][C:34]1[C:39]([F:40])=[C:38]([F:41])[CH:37]=[C:36]([F:42])[C:35]=1[F:43])[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])=[CH:5]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([NH:14][C@H:15]([C:19]([NH:21][CH:22]([C:31](=[O:44])[CH2:32][O:33][C:34]1[C:39]([F:40])=[C:38]([F:41])[CH:37]=[C:36]([F:42])[C:35]=1[F:43])[CH2:23][C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])=[O:20])[CH:16]([CH3:17])[CH3:18])=[O:13])=[CH:5]2
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Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 86756374N-[(5-fluoro-1-methyl-indole-2-cabonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester

Produkt 1

HCID 86756373N-[(5-fluoro-1-methyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of N-[(5-fluoro-1-methyl-indole-2-cabonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (112.6 mg, 0.8 mmol) in CH2Cl2(5.0 ml) was added Dess-Martin periodinane (95 mg, 0.22 mmol) al d the solution stirred for 10 min. at room temperature. The reaction was quenched with Na2S2O4, diluted with EtOAc, washed with NaHCO3, and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography (1:1 EtOAc/hexane) to give the titled product as a white solid (which was directly taken to the next step in Example 115).

Aufarbeitung

  1. customThe reaction was quenched with Na2S2O4
  2. additiondiluted with EtOAc
  3. washwashed with NaHCO3, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography (1:1 EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-13128bc5d8dc4805ba82166ac707d5c5
Quelldatensatz
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06489353B2

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