Benzyl Alcohol → (7-Methoxy-4-oxo-1,4-dihydroquinolin-6-yl)carbamic acid benzyl ester

HRID 387864노트

반응식

HRID 387864 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:13])[CH:8]=[CH:9][NH:10]2)=[CH:5][C:4]=1C(O)=O.[CH2:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C>CN(C)C=O>[CH2:17]([O:24][C:47](=[O:32])[NH:44][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[NH:10][CH:9]=[CH:8][C:7]2=[O:13])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 229364397-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid

생성물 1

HCID 58931364(7-Methoxy-4-oxo-1,4-dihydroquinolin-6-yl)carbamic acid benzyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
95 °C

실험 절차

After dissolving 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid (2.58 g) in N,N-dimethylformamide (50 ml), there were added benzyl alcohol (3.29 ml), diphenylphosphoryl azide 2.51 ml) and triethylamine (1.63 ml), and the mixture was heated and stirred at 95° C. for 5 hours. The reaction solution was poured into saturated saline and extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate and concentrated. The obtained residue was subjected to NH silica gel column chromatography and eluted with a solvent (ethyl acetate:methanol=5:1) to obtain the title compound (2.03 g) as a solid.

후처리

  1. temperaturethe mixture was heated
  2. additionThe reaction solution was poured into saturated saline
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with a solvent (ethyl acetate:methanol=5:1)

출처 및 근거

ORD 기록
ord-259c0c9e42c94f7cb36e04b75029879b
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372981B2

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