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Sodium Hydroxide → N-[(2,6-dichlorophenyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine

HRID 895913
ノート
印刷プレビュー

反応式

HRID 895913 の反応式
C[O:2][C:3](=[O:32])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:31])[N:25]([CH3:30])[CH:26]=[CH:27][C:28]=2[CH3:29])=[CH:19][CH:18]=1)[NH:5][C:6]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])=[O:7].[OH-].[Na+]>C(O)C>[Cl:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([Cl:14])[C:8]=1[C:6]([NH:5][C@H:4]([C:3]([OH:32])=[O:2])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:31])[N:25]([CH3:30])[CH:26]=[CH:27][C:28]=2[CH3:29])=[CH:19][CH:18]=1)=[O:7]
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

4

反応物 2

HCID 14798Sodium HydroxideHCID 69716202N-[(2,6-dichlorophenyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester

生成物 1

HCID 10139365N-[(2,6-dichlorophenyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine収率 92.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
42.5 °C

実験手順

To a suspension of N-[(2,6-dichlorophenyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester (20 mg, 0.04 mmol) in ethanol (1 mL) was added 1N aqueous sodium hydroxide solution (0.5 mL) at room temperature. The mixture was heated to 40-45° C. and stirred for 3 h. Then, the ethanol was removed under vacuum and the residue was diluted with water (10 mL). The aqueous solution was washed with diethyl ether (25 mL) to remove any neutral impurities. The aqueous layer was acidified with 1.0 N HCl and the product was extracted into ethyl acetate (2×25 mL). The combined organic extracts were washed with brine solution (50 mL) and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration afforded 17 mg (89% yield) of N-[(2,6-dichlorophenyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine as an amorphous white solid. ES-HRMS m/e calcd for C23H20Cl2N2O4 (M+Na) 481.0691. found 481.0699.

後処理

  1. customThen, the ethanol was removed under vacuum
  2. additionthe residue was diluted with water (10 mL)
  3. washThe aqueous solution was washed with diethyl ether (25 mL)
  4. customto remove any neutral impurities
  5. extractionthe product was extracted into ethyl acetate (2×25 mL)
  6. washThe combined organic extracts were washed with brine solution (50 mL)
  7. dry with materialwere dried over anhydrous magnesium sulfate
  8. filtrationFiltration of the drying agent and concentration

出典と根拠

ORDレコード
ord-c5f8cf38c3cb4079bb9a3fe765047798
出典データセット
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06916933B2

反応ノート

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