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N-BOC-ethylenediamine → {2-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester

HRID 1410831
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HRID 1410831 반응식
CO[C:3]([C:5]1[C:6]([OH:29])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:8]2)=[O:4].[C:30]([O:34][C:35](=[O:40])[NH:36][CH2:37][CH2:38][NH2:39])([CH3:33])([CH3:32])[CH3:31]>CC(O)=O>[C:30]([O:34][C:35](=[O:40])[NH:36][CH2:37][CH2:38][NH:39][C:3]([C:5]1[C:6]([OH:29])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10](=[O:22])[C:9]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:8]2)=[O:4])([CH3:33])([CH3:31])[CH3:32]
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참가 물질

4

반응물 2

HCID 187201N-BOC-ethylenediamineHCID 682973581-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

생성물 1

HCID 68297633{2-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester수율 106.9%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 1-benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (60 mg, 0.16 mmol) and (2-amino-ethyl)-carbamic acid tert-butyl ester (75 mg, 0.47 mmol) was refluxed for 48 h. After cooling to r.t., AcOH (0.2 mL) was added, and the mixture was concentrated to dryness. The residue was dissolved in EtOAc and washed with 0.1 M HCl, saturated NaHCO3, and brine. The organic layer was dried over MgSO4 and concentrated to give 88 mg of the title compound as a pale yellow solid. MS: (+) m/z 515.30 (M+1).

후처리

  1. temperaturewas refluxed for 48 h
  2. concentrationthe mixture was concentrated to dryness
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 0.1 M HCl, saturated NaHCO3, and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-85bdd51241294299bdebdbd2deb5d55f
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921389B2

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