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Sodium Methoxide → {2-[(7-Benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-ethoxy}-acetic acid

HRID 919764
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인쇄 미리보기

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HRID 919764 반응식
CO[C:3]([C:5]1[N:6]=[C:7]([C:24]#[N:25])[C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4].[NH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]([OH:33])=[O:32].C[O-].[Na+]>CCO>[CH2:16]([N:10]1[C:9](=[O:23])[C:8]2[C:7]([C:24]#[N:25])=[N:6][C:5]([C:3]([NH:26][CH2:27][CH2:28][O:29][CH2:30][C:31]([OH:33])=[O:32])=[O:4])=[C:14]([OH:15])[C:13]=2[CH:12]=[CH:11]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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참가 물질

5

반응물 3

HCID 10942334Sodium MethoxideHCID 111709562-(2-aminoethoxy)acetic AcidHCID 682976087-Benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

생성물 1

HCID 68297143{2-[(7-Benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-ethoxy}-acetic acid수율 12.6%

시약·촉매·용매 1

HCID 702
Ethanol
용매

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온도
150 °C

실험 절차

A mixture of 7-benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (25 mg, 0.075 mmol), (2-amino-ethoxy)-acetic acid (60 mg, 0.50 mmol), and NaOMe (20 mg, 0.37 mmol) in EtOH (5 mL) was refluxed for 16 h, then heated at 150° C. in a microwave reactor for 2 h. Solvent was evaporated in vacuo, and the residue was partitioned between EtOAc and water. 1 M HCl was added with vigorous stilling until pH about 2, and the organic layer was dried over MgSO4 and concentrated. The crude product was purified by chromatography (5-80% EtOAc/hexanes+2% AcOH) to give 4 mg of the title compound as a pale yellow solid. MS: (+) m/z 423.19 (M+1).

후처리

  1. temperaturewas refluxed for 16 h
  2. customSolvent was evaporated in vacuo
  3. customthe residue was partitioned between EtOAc and water
  4. addition1 M HCl was added with vigorous stilling until pH about 2
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography (5-80% EtOAc/hexanes+2% AcOH)

출처 및 근거

ORD 기록
ord-4b281b3f528f44bf848445b1abbf4238
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09271970B2

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