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Triethylamine → 2-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethyl methanesulfonate

HRID 717517
ノート
印刷プレビュー

反応式

HRID 717517 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25][OH:26])=[CH:21][CH:20]=1)[C:13]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:31][CH:30]=1)=[C:12]2[CH3:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:51][S:52](Cl)(=[O:54])=[O:53]>C(Cl)Cl>[CH3:51][S:52]([O:26][CH2:25][CH2:24][O:23][C:22]1[CH:27]=[CH:28][C:19]([CH2:18][N:14]2[C:15]3[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:17][CH:16]=3)[C:12]([CH3:43])=[C:13]2[C:29]2[CH:30]=[CH:31][C:32]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:33][CH:34]=2)=[CH:20][CH:21]=1)(=[O:54])=[O:53]
参加物反応条件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 121331372-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethanol

生成物 1

HCID 893071282-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethyl methanesulfonate収率 96%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

反応条件

温度
0 °C

実験手順

A solution of 2-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethanol (546 mg, 0.96 mmol) in DCM (10 mL) was cooled to 0° C. Triethylamine (0.2 mL, 1.43 mmol) and methanesulfonyl chloride (0.1 mL, 1.29 mmol) were added and the reaction was stirred at 0° C. for 1 h. The reaction was diluted with DCM (30 mL) and then washed with 1M HCl (20 mL), washed with water (20 mL), dried (MgSO4), filtered and concentrated under vacuum to give 597 mg of 2-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethyl methanesulfonate as a yellow foam. 1H NMR (400 MHz, DMSO-d6): δ 7.48 (d, 4H), 7.44-7.37 (m, 4H), 7.37-7.32 (m, 2H), 7.30 (d, 2H), 7.21 (d, 1H), 7.15-7.10 (m, 3H), 6.83-6.74 (m, 5H), 5.20-5.10 (m, 6H), 4.50-4.45 (m, 2H), 4.17-4.11 (m, 2H), 2.16 (s, 3H). LCMS: 648.1 (M+H)+.

後処理

  1. washwashed with 1M HCl (20 mL)
  2. washwashed with water (20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-9c0959306ed14181a754db85bfb4495a
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09193714B2

反応ノート

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