Water → 2,5,6-Trichloro-3-[N-(methoxycarbonylamino)iminomethylidene]-1-(beta-D-ribofuranosyl)indole

HRID 28352

Reaktionsgleichung

Reaktionsgleichung von HRID 28352
[Cl:1][C:2]1[N:3]([C@@H:15]2[O:21][C@H:20]([CH2:22][OH:23])[C@@H:18]([OH:19])[C@H:16]2[OH:17])[C:4]2[C:9]([C:10]=1[CH:11]=O)=[CH:8][C:7]([Cl:13])=[C:6]([Cl:14])[CH:5]=2.[NH:24]([C:26]([O:28][CH3:29])=[O:27])[NH2:25].O>CO>[Cl:1][CH:2]1[C:10](=[C:11]=[N:25][NH:24][C:26]([O:28][CH3:29])=[O:27])[C:9]2[C:4](=[CH:5][C:6]([Cl:14])=[C:7]([Cl:13])[CH:8]=2)[N:3]1[C@@H:15]1[O:21][C@H:20]([CH2:22][OH:23])[C@@H:18]([OH:19])[C@H:16]1[OH:17]

Komponenten

5

Edukt 3

HCID 962WaterHCID 80519Methyl carbazateHCID 3011610Ftcri

Produkt 1

HCID 865989702,5,6-Trichloro-3-[N-(methoxycarbonylamino)iminomethylidene]-1-(beta-D-ribofuranosyl)indoleAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2,5,6-Trichloro-3-formyl-1-(β-D-ribofuranosyl)indole (4.3, 122 mg, 0.32 mmol) was dissolved in MeOH (10 mL) to which was added methyl hydrazinocarboxylate (115 mg, 1.3 mmol). The resulting solution was heated on a 60 C oil bath for 16 h, then cooled to room temperature and poured into 100 mL of water, and the solvent evaporated to approx 50 mL. The resulting suspension was cooled to 4C, then filtered and the solids rinsed with cold water (25 mL). The solids were recrystallized from boiling EtOAc/hexane to yield 123 mg (85%) of 4.31 as a pale pink crystalline solid: mp 217-219 C; Rf 0.2 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 11.17 (b, 1H, D2O exch.), 8.54 (s, 1H), 8.42 (s, 1H), 8.22 (b, 1H), 5.92 (d, 1H), 5.42-5.37 (m, 2H, D2O exch.), 5.25 (d, 1H, D2O exch.), 4.43 (q, 1H), 4.15 (d, 1H), 3.98 (d, 1H), 3.72 (b, 5H). 13C-NMR (125 MHz, DMSO-d6): δ 153.88, 133.17, 129.33, 126.08, 124.96, 124.06, 122.17, 115.34, 108.59, 88.76, 86.03, 71.30, 69.73, 69.62, 61.07, 52.04. HRMS (ES) m/z calcd. for C16H16Cl3N3O6·Na 474.0002, found 473.9999. Anal calcd for C16H16Cl3N3O6·¼H2O: C, 42.03; H, 3.64; N, 9.19. Found: C, 42.11; H, 3.92; N, 9.18.

Aufarbeitung

  1. temperatureThe resulting solution was heated on a 60 C oil bath for 16 h
  2. customthe solvent evaporated to approx 50 mL
  3. temperatureThe resulting suspension was cooled to 4C
  4. filtrationfiltered
  5. washthe solids rinsed with cold water (25 mL)
  6. customThe solids were recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-723df91f03f94b6992372177f3519484
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419963B2

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