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Diisopropylethylamine → tert-Butyl N-((5-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

HRID 1868836
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HRID 1868836 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:20])=[C:5]([C:15](OCC)=[O:16])[C:6](=[O:14])[C:7]2([CH3:13])[CH3:12].Cl.[C:22]([O:26][C:27](=[O:30])[CH2:28][NH2:29])([CH3:25])([CH3:24])[CH3:23].CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:20])=[C:5]([C:15]([NH:29][CH2:28][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:30])=[O:16])[C:6](=[O:14])[C:7]2([CH3:13])[CH3:12]
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099489Ethyl 5-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate

생성물 1

HCID 86629259tert-Butyl N-((5-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate수율 75.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane
용매

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온도
75 °C

실험 절차

Ethyl 5-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (210 mg, 713 μmol, 1.0 eq) and glycine tert-butyl ester hydrochloride (143 mg, 855 μmol, 1.20 eq) were mixed in dioxane (5 mL) in a round bottom flask. DIPEA (186 μL, 1069 μmol, 1.5 eq) was added via syringe, and the reaction was stirred at 75° C. for 4 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo to give a yellow solid. The crude product was purified by silica flash chromatography (0-50% DCM/hexane) to give the desired compound as a white solid (204 mg). MS m/e=380 (M+H)+.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto give a yellow solid
  4. customThe crude product was purified by silica flash chromatography (0-50% DCM/hexane)

출처 및 근거

ORD 기록
ord-9d48c6af54074b2caf93608a0625f4f8
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07635715B2

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