Hydrochloric Acid → 7-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

HRID 919715노트

반응식

HRID 919715 반응식
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8](=[O:19])[C:7]=1[CH2:20][N:21]([CH2:32][C:33]([O:35][CH3:36])=[O:34])S(C1C=CC(C)=CC=1)(=O)=O)=O)C.C[O-].[Na+].Cl>CO.[Cl-].[Na+].O>[CH3:36][O:35][C:33]([C:32]1[N:21]=[CH:20][C:7]2[C:8](=[O:19])[N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[CH:11][C:6]=2[C:4]=1[OH:3])=[O:34]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 682976751-Benzyl-3-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid ethyl ester

생성물 1

HCID 682977357-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester수율 85.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 57417360Sodium chloride; water용매

실험 절차

1-Benzyl-3-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid ethyl ester (232 mg, 0.45 mmol) was dissolved in MeOH (10 mL). NaOMe solution (0.32 mL, 1.36 mmol, 25 wt % in MeOH) was added, and the mixture was stirred overnight. Brine (20 mL) was added, followed by 1M HCl until pH was about 4. The resulting suspension was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The residue was chromatographed (5-60% EtOAc/hexanes+2% AcOH) to give 119 mg of the title compound as a yellow solid. MS: (+) m/z 311.13 (M+1).

후처리

  1. extractionThe resulting suspension was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was chromatographed (5-60% EtOAc/hexanes+2% AcOH)

출처 및 근거

ORD 기록
ord-3502c7356027452298d07944dc557b07
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09271970B2

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