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Sodium Iodide → 2-Methyl-2-[(1-phenethyloxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-propionic acid methyl ester

HRID 874744
ノート
印刷プレビュー

反応式

HRID 874744 の反応式
[CH3:1][O:2][C:3](=[O:21])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]=1[OH:20])=[O:9])([CH3:6])[CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[I-].[Na+]>CN(C)C=O.O.C(OCC)C>[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:6])([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]=1[O:20][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:9])[CH3:5]
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

8

反応物 4

HCID 5238Sodium IodideHCID 7666Phenethyl bromideHCID 10796Cesium carbonateHCID 57912188HCID 57912188、化合物

生成物 1

HCID 688447242-Methyl-2-[(1-phenethyloxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-propionic acid methyl ester収率 63.5%

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 3283Diethyl Ether溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

80 mg 2-[(1-hydroxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-2-methyl-pro-pionic acid methyl ester, 224 mg cesium carbonate, 61 mg of (2-bromoethyl)-benzene and 4 mg sodium iodide were dissolved in 5 ml of N,N-dimethylformamide and stirred at 80° C. for 6 h. 10 ml of diethyl ether and 10 ml of water were added to the reaction. The organic layer was separated and washed again with 10 ml of water. It was then dried over magnesium sulphate, filtered and concentrated in vacuo. Purification by flash chromatography (silica, heptanes/ethyl acetate) afforded 69 mg of 2-methyl-2-[(1-phenethyloxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-propionic acid methyl ester.

後処理

  1. customThe organic layer was separated
  2. washwashed again with 10 ml of water
  3. dry with materialIt was then dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (silica, heptanes/ethyl acetate)

出典と根拠

ORDレコード
ord-c1ada699085743b69283b672e455f424
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08980938B2

反応ノート

読み込み中…

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