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Potassium Carbonate → (R)-2-[2,4-dioxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid methyl ester

HRID 388473
ノート
印刷プレビュー

反応式

HRID 388473 の反応式
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:19])[CH2:5][CH2:6][CH3:7].C[C:22]1[C:23]([CH3:38])=[C:24](C)[C:25]([CH3:36])=[C:26]2[C:30]=1[N:29]([CH3:31])[C:28](C)=[C:27]2[CH2:33]NI.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:33][C:27]2[C:26]3[C:30](=[CH:22][C:23]([CH3:38])=[CH:24][C:25]=3[CH3:36])[N:29]([CH3:31])[CH:28]=2)[C:9]1=[O:19])[CH2:5][CH2:6][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 11430Potassium CarbonateHCID 68726798(R)-2-(2,4-Dioxo-1,4-dihydro-2H-quinazolin-3-yl)-pentanoic acid methyl esterHCID 131730211trimethyl-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-amino iodide

生成物 1

HCID 68745323(R)-2-[2,4-dioxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid methyl ester収率 80.7%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
100 °C

実験手順

To a solution of (R)-2-(2,4-Dioxo-1,4-dihydro-2H-quinazolin-3-yl)-pentanoic acid methyl ester (50 mg, 0.18 mmol) (prepared according to example 1, steps 1-3) in DMF (10 mL) are added trimethyl-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-amino iodide (97 mg, 0.27 mmol) and K2CO3 (50 mg, 0.36 mmol) at room temperature. The solution is heated to 100° C. for 4 hours. The solution is cooled and is extracted with water and EtOAc. The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by flash chromatography with 20% EtOAc in Hexane as the eluent to afford (R)-2-[2,4-dioxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid methyl ester (65 mg, 80%) as a white foam.

後処理

  1. temperatureThe solution is cooled
  2. extractionis extracted with water and EtOAc
  3. dry with materialThe combined organic layer is dried with MgSO4
  4. filtrationis filtered
  5. concentrationThe filtrate is concentrated
  6. customthe residue is purified by flash chromatography with 20% EtOAc in Hexane as the eluent

出典と根拠

ORDレコード
ord-8e2484668a184771af1b0793a73d1ee9
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08377949B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート