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Hydrochloric Acid → [5-Benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetic acid

HRID 1349484
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HRID 1349484 반응식
[CH2:1]([O:8][C:9]1[C:10](=[O:37])[C:11]([CH2:32][C:33]([O:35]C)=[O:34])=[CH:12][N:13]([CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29])[C:14]=1[C:15](=[O:25])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+].Cl>O1CCCC1.O>[CH2:1]([O:8][C:9]1[C:10](=[O:37])[C:11]([CH2:32][C:33]([OH:35])=[O:34])=[CH:12][N:13]([CH2:26][CH:27]([O:28][CH3:29])[O:30][CH3:31])[C:14]=1[C:15](=[O:25])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 58859124Methyl[5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetate

생성물 1

HCID 21091365[5-Benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetic acid수율 79.4%

시약·촉매·용매

2
HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

To a solution of methyl [5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetate (150 mg) obtained in Example 187, Step 1 in tetrahydrofuran (1.5 ml)-methanol (1.5 ml) was added 4N aqueous sodium hydroxide solution (0.11 ml), and the mixture was stirred at 70° C. for 30 min. The reaction mixture was warmed to room temperature, 1N aqueous hydrochloric acid (0.5 ml) and water (15 ml) were added, and the mixture was extracted twice with ethyl acetate (30 ml each). The ethyl acetate layer was washed with water, dried, concentrated, and crystallized from ethyl acetate-diisopropyl ether to give [5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetic acid (116 mg).

후처리

  1. temperatureThe reaction mixture was warmed to room temperature
  2. extractionthe mixture was extracted twice with ethyl acetate (30 ml each)
  3. washThe ethyl acetate layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customcrystallized from ethyl acetate-diisopropyl ether

출처 및 근거

ORD 기록
ord-6bfc5b8510b8411aa4f75339b0cba27e
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07211572B2

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