Sodium Hydroxide → 2-[6-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylcarbamoyl]morpholine-4-carboxylic acid tert-butyl ester

HRID 1401868ノート

反応式

HRID 1401868 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C.[CH3:35][C:36]1([CH3:55])[CH2:45][CH2:44][C:43]([CH3:47])([CH3:46])[C:42]2[CH:41]=[C:40]([C:48]3[N:53]=[C:52]([NH2:54])[CH:51]=[CH:50][CH:49]=3)[CH:39]=[CH:38][C:37]1=2.[OH-].[Na+]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14](=[O:16])[NH:54][C:52]2[CH:51]=[CH:50][CH:49]=[C:48]([C:40]3[CH:39]=[CH:38][C:37]4[C:36]([CH3:55])([CH3:35])[CH2:45][CH2:44][C:43]([CH3:47])([CH3:46])[C:42]=4[CH:41]=3)[N:53]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 673240416-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylamine

生成物 1

HCID 673232752-[6-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylcarbamoyl]morpholine-4-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

82 mg (0.36 mmol) of morpholine-2,4-dicarboxylic acid 4-tert-butyl ester and 97 mg (0.39 mmol) of ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate (EEDQ) are suspended in 2 ml of THF and stirred at room temperature for 20 min. 100 mg (0.36 mmol) of 6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylamine from step a are added to the mixture. The mixture is stirred further overnight, water is added, the mixture is adjusted to pH 9-10 using a 2N NaOH solution and extracted twice with EA. The combined organic phases are dried, filtered and evaporated (191 mg). The residue is purified by means of flash chromatography on silica gel.

後処理

  1. stirringThe mixture is stirred further overnight
  2. extractionextracted twice with EA
  3. customThe combined organic phases are dried
  4. filtrationfiltered
  5. customevaporated (191 mg)
  6. customThe residue is purified by means of flash chromatography on silica gel

出典と根拠

ORDレコード
ord-cecd65411c414631b210db514b9a7695
出典データセット
uspto-grants-2014_12
特許番号
US08907098B2

反応ノート

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