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

HRID 1410718ノート

反応式

HRID 1410718 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-787cd0f0588c469ea12486f461c34280
出典データセット
uspto-grants-2014_12
特許番号
US08921389B2

反応ノート

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