Triethylamine → [(S)-2-((S)-8-Azidomethyl-7,8-dihydro-[1,4]dioxino[2,3-g]indazol-1-yl)-1-methyl-ethyl]-carbamic acid tert-butyl ester

HRID 31368

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]([CH3:25])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]3[O:22][CH2:21][C@H:20]([CH2:23]O)[O:19][C:17]3=2)[CH:12]=[N:11]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[N-:43]=[N+:44]=[N-:45].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.CS(C)=O>[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]([CH3:25])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]3[O:22][CH2:21][C@H:20]([CH2:23][N:43]=[N+:44]=[N-:45])[O:19][C:17]3=2)[CH:12]=[N:11]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a 0° C. stirred solution of the alcohol from Step A (0.69 g, 1.87 mmol) in anhydrous tetrahydrofuran (30 mL) was added triethylamine (0.38 g, 0.52 mL, 3.7 mmol) and methanesulfonic anhydride (0.49 g, 2.81 mmol) under a nitrogen atmosphere. After 1 h the volatiles were evaporated. To the residue was added anhydrous DMSO (40 mL) and sodium azide (2.43 g, 37 mmol). The resulting mixture was heated at 90° C. for 1 h, cooled, mixed with a saturated aqueous solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate (50 mL×3). Chromatography on silica eluting with a gradient of 0% to 25% ethyl acetate/hexane gave an oil (0.65 g, 88%), that solidified on standing. Crystallization from ethyl acetate/hexane gave a crystalline solid (0.48 g, 65%): mp 134-135° C. LCMS (+APCI) 395 (M+H).

Aufarbeitung

customAfter 1 h the volatiles were evaporated
temperaturecooled
extractionextracted with ethyl acetate (50 mL×3)

Quellen und Nachweise

ORD-Eintrag: ord-085b03b4c67c420eb92635522fe99a89
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07425572B2

Verknüpfte Notizen

Wird geladen…