Benzyl N-(tert-butoxycarbonyl)-4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-L-phenylalaninate → (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid

HRID 724705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724705
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:29]([O:31]CC1C=CC=CC=1)=[O:30])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:21](=[O:23])(=[O:22])[N:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:19](=[O:28])[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[S:21](=[O:22])(=[O:23])[N:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:19](=[O:28])[CH2:18]2)=[CH:13][CH:12]=1)[C:29]([OH:31])=[O:30])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 11720867Benzyl N-(tert-butoxycarbonyl)-4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-L-phenylalaninate

Produkt 1

HCID 11568707(2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acidAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of benzyl N-(tert-butoxycarbonyl)-4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-L-phenylalaninate (1.3 g, 2.4 mmol) in ethanol (35 mL) in a parr shaker, palladium (0.700 g, 6.58 mmol) (Pd, 10% by weight on activated carbon) was added and hydrogenated overnight at 50 psi. The suspension was filtered through celite and concentrated to give the crude product. The crude was purified on preparative LCMS to give the product (0.71 g, 65%). LCMS found for C21H3N2O7S (M+H)+: m/z=455.

Aufarbeitung

  1. filtrationThe suspension was filtered through celite and
  2. concentrationconcentrated
  3. customto give the crude product
  4. customThe crude was purified on preparative LCMS

Quellen und Nachweise

ORD-Eintrag
ord-bc173ea7b91f4bc6a8a4c22ac6bedf82
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141596B2

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