Benzylamine → HCID 10871345、化合物

HRID 928873ノート

反応式

HRID 928873 の反応式
C([O:4][CH:5]1[O:22][C@H:21]([C:23]([O:25][CH3:26])=[O:24])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C(N)C1C=CC=CC=1>CN(C=O)C>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([C:23]([O:25][CH3:26])=[O:24])[O:22][CH:5]1[OH:4])(=[O:10])[CH3:9]

参加物

4

反応物 2

HCID 7504BenzylamineHCID 11047049Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate

生成物 1

HCID 10871345HCID 10871345、化合物収率 84%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate F13-2 (1.2 g, 3.2 mmol) was dissolved in dry DMF (10 mL) under N2. To the solution, benzylamine (0.42 mL, 3.8 mmol) was added. The mixture was stirred at r.t. for 16 hours. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (Hexane:EtOAc=1:2, by volume) to afford a white solid F13c in 84% yield. 1H NMR (600 MHz, CDCl3) δ 5.50-5.55 (m, 1H), 5.11-5.27 (m, 1H), 4.85-4.91 (m, 1H), 5.39-4.56 (m, 2H), 3.70-3.72 (m, 3H), 1.99-2.05 (m, 9H). 13C NMR (150 MHz, CDCl3) δ 170.68, 170.45, 170.34, 170.30, 169.94, 169.81, 168.77, 167.83, 95.59, 90.36, 72.98, 72.66, 71.81, 70.97, 69.73, 69.61, 69.34, 68.12, 53.21, 53.11, 20.85, 20.84, 20.77, 20.70, 20.66, 20.65.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (Hexane:EtOAc=1:2, by volume)
  3. customto afford a white solid F13c in 84% yield

出典と根拠

ORDレコード
ord-f3dc00089e5f4777b5757fc6d398f3d2
出典データセット
uspto-grants-2016_03
特許番号
US09290530B2

反応ノート

読み込み中…