Benzylamine → HCID 10871345, 화합물

HRID 928873노트

반응식

HRID 928873 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 10871345HCID 10871345, 화합물수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f3dc00089e5f4777b5757fc6d398f3d2
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290530B2

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