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

HRID 2297069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2297069
[C:1]([O:5][C:6]([CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:18]([NH:20][C@H:21]([C:25]([NH:27][CH:28]([CH:37]([OH:50])[CH2:38][O:39][C:40]1[C:45]([F:46])=[C:44]([F:47])[CH:43]=[C:42]([F:48])[C:41]=1[F:49])[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:18]([NH:20][C@H:21]([C:25]([NH:27][CH:28]([C:37](=[O:50])[CH2:38][O:39][C:40]1[C:45]([F:46])=[C:44]([F:47])[CH:43]=[C:42]([F:48])[C:41]=1[F:49])[CH2:29][C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 86756375N-{[1-(tert-butyl)oxycarbonylmethyl-indole-2-cabonyl]valinyl}-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

Produkt 1

HCID 86756376N-{[1-(tert-butyl)oxycarbonylmethyl-indole-2-cabonyl]valinyl}-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl EsterAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-{[1-(tert-butyl)oxycarbonylmethyl-indole-2-cabonyl]valinyl}-3-amino4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (290 mg, 0.42 mmol) in CH2Cl2(5.0 ml) was added Dess-Martin periodinane (204 mg, 0.48 mmol) and 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 (235 mg, 82%).

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-a54b9a265c5b4b00a614b352f6dead43
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489353B2

Notizen zur Reaktion

Wird geladen…