Hydrogen Peroxide → (6S,8R)-8-allyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid

HRID 10990

Reaktionsgleichung

[CH2:1]([O:8][C:9](=[O:43])[N:10]([CH2:40][CH:41]=[CH2:42])[C:11]1[C:16](=O)[N:15]2[C@H:18]([C:24](N(C(OC(C)(C)C)=O)C3C=CC=CC=3)=[O:25])[CH2:19][C@@H:20]([CH2:21][CH:22]=[CH2:23])[C:14]2=[N:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.[Li+].[OH-:47].[O-:48]S([O-])=O.[Na+].[Na+]>C1COCC1.O.O>[CH2:21]([C@H:20]1[C:14]2=[N:13][CH:12]=[C:11]([N:10]([CH2:40][CH:41]=[CH2:42])[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:43])[C:16](=[O:47])[N:15]2[C@H:18]([C:24]([OH:48])=[O:25])[CH2:19]1)[CH:22]=[CH2:23]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 28c (311 mg, 0.532 mmol) in 5 mL THF/H2O (4:1) at 0° C., were added 30% H2O2 (0.241 mL, 2.13 mmol) and IM LiOH (0.851 mL, 0.851 mmol). The mixture was stirred at 0° C. for 2 h, then Na2SO3 and 10 mL H2O were added. The organic solvent was evaporated under a stream of nitrogen. The precipitate was filtered and rinsed with H2O and 0.1 N NaOH. The combined aqueous filtrate was acidified with conc. HCl, then extracted with EtOAc (3×). The combined organic extract was washed with brine, dried (Na2SO4), and concentrated to afford 208 mg (96%) of 28d. MS (ESI) 410.3 (M+H+), 432.3 (M+Na+), 408.2 (M−H+).

Aufarbeitung

customThe organic solvent was evaporated under a stream of nitrogen
filtrationThe precipitate was filtered
washrinsed with H2O and 0.1 N NaOH
extractionextracted with EtOAc (3×)
extractionThe combined organic extract
washwas washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-f51d0ab866974f10b8c0efcd2b1d03dd
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07094783B2

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