Diisopropylethylamine → 1,1-Dimethylethyl N-((7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

HRID 1868761

반응식

HRID 1868761 반응식
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([OH:29])=[C:16]([C:24](OCC)=[O:25])[C:17](=[O:23])[C:18]2([CH3:22])[CH3:21])=[CH:13][CH:12]=1.Cl.[C:31]([O:35][C:36](=[O:39])[CH2:37][NH2:38])([CH3:34])([CH3:33])[CH3:32]>O1CCOCC1.CCOCC>[Br:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([OH:29])=[C:16]([C:24]([NH:38][CH2:37][C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:39])=[O:25])[C:17](=[O:23])[C:18]2([CH3:22])[CH3:21])=[CH:13][CH:12]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099405HCID 67099405, 화합물

생성물 1

HCID 670997641,1-Dimethylethyl N-((7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate수율 83.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

DIPEA (3.86 mL, 22.2 mmol, 1.2 eq) was added to a mixture of ethyl 7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (6.27 g, 18.5 mmol) and glycine tert-butyl ester hydrochloride (3.72 g, 22.2 mmol) in dioxane (30 mL). The reaction mixture was stirred at 85° C. for 3 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo to give a light yellow solid. The crude solid was suspended in ether, filtered, and washed with water to give the desired ester as a white solid (6.53 g). MS (m/e)=368.1 (M+H-tBu)+.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto give a light yellow solid
  4. filtrationfiltered
  5. washwashed with water

출처 및 근거

ORD 기록
ord-ac50e6ed9cc149fba1cd8c59422cbb20
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635715B2

연결된 노트

불러오는 중…