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 1401868노트

반응식

HRID 1401868 반응식
[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]

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cecd65411c414631b210db514b9a7695
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08907098B2

반응 노트

불러오는 중…