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Ethyl Bromide → [3-(Anthracen-9-ylmethyl-ethyl-amino)-propyl]-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester

HRID 12994
ノート
印刷プレビュー

反応式

HRID 12994 の反応式
[CH2:1](Br)[CH3:2].[C:4]([O:8][C:9](=[O:41])[N:10]([CH2:22][CH2:23][CH2:24][NH:25][CH2:26][C:27]1[C:28]2[C:33]([CH:34]=[C:35]3[C:40]=1[CH:39]=[CH:38][CH:37]=[CH:36]3)=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:7])([CH3:6])[CH3:5].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:4]([O:8][C:9](=[O:41])[N:10]([CH2:22][CH2:23][CH2:24][N:25]([CH2:26][C:27]1[C:40]2[C:35]([CH:34]=[C:33]3[C:28]=1[CH:29]=[CH:30][CH:31]=[CH:32]3)=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:1][CH3:2])[CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])([CH3:5])([CH3:6])[CH3:7]
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 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 11720576{3-[(Anthracen-9-ylmethyl)-amino]-propyl}-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester

生成物 1

HCID 11497655[3-(Anthracen-9-ylmethyl-ethyl-amino)-propyl]-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester収率 80%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

反応条件

温度
75 °C

実験手順

Ethylbromide (EtBr, 508 mg, 4.66 mmol) was dissolved in anhydrous acetonitrile and added to a stirring mixture of compound 10 (805 mg, 1.55 mmol) and anhydrous K2CO3 (644 mg, 4.66 mmol). The mixture was then stirred overnight at 75° C. under a N2 atmosphere. After the confirmation of the disappearance of the 10 by TLC, the solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (20 mL) and washed three times with aqueous sodium carbonate. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. Flash column chromatography of the residue gave 11 as a light yellow oil. Yield 80%; Rf=0.35 (3% MeOH/CHCl3); 1H NMR (CDCl3) δ 8.43 (d, 2H), 8.25 (s, 1H), 7.86 (d, 2H), 7.43 (m, 2H), 7.37 (m, 2H), 4.34 (s, 2H), 2.78-2.92 (m, 4H), 2.64 (m, 4H), 2.36 (m, 2H), 1.21-1.48 (m, 23H), 1.16 (m, 2H); 13C NMR (CDCl3) δ 155.7, 131.1 (3C), 131.0, 128.7 (2C), 127.0 (2C), 125.2 (2C), 124.8 (2C), 124.5 (2C), 78.9, 78.4, 53.4, 50.6, 50.0, 47.9, 45.3, 43.5, 37.1, 28.3 (6C), 26.5, 11.7. HRMS (FAB) m/z calcd. for C33H47N3O4 (M+H)+ 550.3639, found 550.3619.

後処理

  1. concentrationAfter the confirmation of the disappearance of the 10 by TLC, the solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  3. washwashed three times with aqueous sodium carbonate
  4. customThe organic layer was separated
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-a36cc7035a194b5b81c93cb9fe910fe6
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07728041B2

反応ノート

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