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

HRID 28352

反応式

HRID 28352 の反応式
[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]

参加物

5

反応物 3

HCID 962WaterHCID 80519Methyl carbazateHCID 3011610Ftcri

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-723df91f03f94b6992372177f3519484
出典データセット
uspto-grants-2008_09
特許番号
US07419963B2

関連ノート

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