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Sodium Methoxide → {2-[(7-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-ethoxy}-acetic acid

HRID 1410807
ノート
印刷プレビュー

反応式

HRID 1410807 の反応式
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4].[NH2:24][CH2:25][CH2:26][O:27][CH2:28][C:29]([OH:31])=[O:30].C[O-].[Na+]>CO.C([O-])(O)=O.[Na+]>[CH2:16]([N:10]1[C:9](=[O:23])[C:8]2[CH:7]=[N:6][C:5]([C:3]([NH:24][CH2:25][CH2:26][O:27][CH2:28][C:29]([OH:31])=[O:30])=[O:4])=[C:14]([OH:15])[C:13]=2[CH:12]=[CH:11]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10942334Sodium MethoxideHCID 111709562-(2-aminoethoxy)acetic AcidHCID 682977357-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

生成物 1

HCID 60151262{2-[(7-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-ethoxy}-acetic acid収率 32.1%

試薬・触媒・溶媒 2

HCID 887Methanol
溶媒
HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
140 °C

実験手順

A mixture of 7-benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (20 mg, 0.065 mmol), (2-amino-ethoxy)-acetic acid (39 mg, 0.32 mmol), and NaOMe (14 mg, 0.26 mmol) in MeOH (2 mL) was heated at 140° C. in a microwave reactor for 6 h. Solvent was evaporated in vacuo, and the residue was partitioned between EtOAc and water. 1 M HCl was added with vigorous stirring until pH about 1, and the organic layer was dried over MgSO4 and concentrated. The crude product was purified by chromatography (0-2% MeOH/EtOAc+1% AcOH) to give a yellow solid. The solid was then dissolved in saturated NaHCO3 and washed several times with ether. The aqueous layer was acidified to pH about 1 with 4 M HCl, and the resulting precipitate was collected by filtration and dried to give 8.3 mg of the title compound as an off-white solid. MS: (+) m/z 398.29 (M+1).

後処理

  1. customSolvent was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. addition1 M HCl was added
  4. dry with materialthe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography (0-2% MeOH/EtOAc+1% AcOH)
  7. customto give a yellow solid
  8. washwashed several times with ether
  9. filtrationthe resulting precipitate was collected by filtration
  10. customdried

出典と根拠

ORDレコード
ord-93e447a479634035b5d0dc2a6bc272b5
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921389B2

反応ノート

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