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

HRID 919754ノート

反応式

HRID 919754 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7540665224be4b10b1f0cfea00ddc48e
出典データセット
uspto-grants-2016_03
特許番号
US09271970B2

反応ノート

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