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Triethylamine → (3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl methanesulfonate

HRID 1625937
ノート
印刷プレビュー

反応式

HRID 1625937 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:9][C@@H:10]1[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:36]([O:42][C:43](=[O:45])[CH3:44])[C@@H:35]([CH2:46][O:47][C:48](=[O:50])[CH3:49])[O:34][C@H:11]1[O:12][C:13]1[C:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH2:27][CH2:28][OH:29])=[CH:21][C:20]=2[CH3:30])=[C:16]([CH:31]([CH3:33])[CH3:32])[NH:15][N:14]=1)(=[O:8])[CH3:7].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:29][CH2:28][CH2:27]/[CH:26]=[CH:25]/[C:22]1[CH:23]=[CH:24][C:19]([CH2:18][C:17]2[C:13]([O:12][C@@H:11]3[O:34][C@H:35]([CH2:46][O:47][C:48](=[O:50])[CH3:49])[C@@H:36]([O:42][C:43](=[O:45])[CH3:44])[C@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:10]3[O:9][C:6](=[O:8])[CH3:7])=[N:14][NH:15][C:16]=2[CH:31]([CH3:33])[CH3:32])=[C:20]([CH3:30])[CH:21]=1)(=[O:4])=[O:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 867151534-{4-[(1E)-4-hydroxybut-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

生成物 1

HCID 86701862(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl methanesulfonate収率 320.2%

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒

実験手順

Add methanesulfonyl chloride (1.35 g, 11.8 mmol) to a solution of 4-{4-[(1E)-4-hydroxybut-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (1.5 g, 2.38 mmol) and triethylamine (5 g, 49.2 mmol) in dichloromethane (50 mL) at 0° C. After 30 minutes at room temperature, extract with dichloromethane (80 mL), and wash with water (80 mL) and brine (40 mL). Dry organic phase over sodium sulfate, filter and concentrate under reduced pressure. Purify the resulting residue by flash chromatography (silica gel, gradient ethyl acetate/dichloromethane from 10-65% over 20 min, 120 g column) to yield the title compound (5.4 g, 7.62 mmol). MS (m/z): 708.5 (M+1), 706.5 (M−1).

後処理

  1. extractionextract with dichloromethane (80 mL)
  2. washwash with water (80 mL) and brine (40 mL)
  3. filtrationDry organic phase over sodium sulfate, filter
  4. concentrationconcentrate under reduced pressure
  5. customPurify the resulting residue by flash chromatography (silica gel, gradient ethyl acetate/dichloromethane from 10-65% over 20 min, 120 g column)

出典と根拠

ORDレコード
ord-42383dcb756f498c818c82acbd1a8d62
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785404B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート