Hydrochloric Acid → Methyl 6-benzyl-4-hydroxy-5-oxo-5,6-dihydro-2,6-naphthyridine-3-carboxylate

HRID 1410757노트

반응식

HRID 1410757 반응식
C([O:3][C:4]([C:6]1[C:7](=[O:36])[N:8]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:9]=[CH:10][C:11]=1[CH2:12][N:13]([CH2:24][C:25]([O:27][CH3:28])=[O:26])S(C1C=CC(C)=CC=1)(=O)=O)=O)C.C[O-].[Na+].Cl>CO>[CH3:28][O:27][C:25]([C:24]1[N:13]=[CH:12][C:11]2[CH:10]=[CH:9][N:8]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:7](=[O:36])[C:6]=2[C:4]=1[OH:3])=[O:26]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 682972301-Benzyl-4-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester

생성물 1

HCID 68297693Methyl 6-benzyl-4-hydroxy-5-oxo-5,6-dihydro-2,6-naphthyridine-3-carboxylate수율 32.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

1-Benzyl-4-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester (0.94 g, 1.84 mmol) was dissolved in MeOH (40 mL) and cooled in an ice bath. NaOMe solution (1.3 mL, 5.51 mmol, 25 wt % in MeOH) was added, and the mixture was stirred overnight. The mixture was placed in an ice bath, and 1 M HCl was added until pH was about 3-4. The resulting suspension was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The residue was chromatographed (5-90% EtOAc/hexanes+2% AcOH) to give 183 mg of the title compound as an orange solid. MS: (−) m/z 309.01 (M−1).

후처리

  1. temperaturecooled in an ice bath
  2. customThe mixture was placed in an ice bath
  3. extractionThe resulting suspension was extracted with CH2Cl2
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed (5-90% EtOAc/hexanes+2% AcOH)

출처 및 근거

ORD 기록
ord-206267366ff242e084a42aef8271d8ac
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921389B2

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