Sodium Hydroxide → N-[(2-chloro-6-ethylphenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine

HRID 844858ノート

反応式

HRID 844858 の反応式
C[O:2][C:3](=[O:35])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25](=[O:34])[N:26]([CH3:33])[C:27](=[O:32])[N:28]([CH3:31])[C:29]=2[CH3:30])=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1[C:13]([CH2:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:16])=[O:7].[OH-].[Na+]>C(O)C>[Cl:16][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([CH2:14][CH3:15])[C:8]=1[C:6]([NH:5][C@H:4]([C:3]([OH:35])=[O:2])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[C:25](=[O:34])[N:26]([CH3:33])[C:27](=[O:32])[N:28]([CH3:31])[C:29]=2[CH3:30])=[CH:22][CH:23]=1)=[O:7]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 69335943N-[(2-chloro-6-ethylphenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester

生成物 1

HCID 69336784N-[(2-chloro-6-ethylphenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine収率 87%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of N-[(2-chloro-6-ethylphenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester (0.33 mmol, 164 mg) in ethanol (2 mL) was added aqueous 1.0 N sodium hydroxide (0.7 mL) at room temperature. The mixture was stirred for 3 h at room temperature. The ethanol was removed under reduced pressure and the residue was diluted with water (30 mL). The aqueous solution was washed with diethyl ether (30 mL) to remove any neutral impurities. The aqueous layer was acidified with 1.0 N HCl and the product was extracted into ethyl acetate (2×35 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 of the filtrate afforded 138 mg (87% yield) of N-[(2-chloro-6-ethylphenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine as a white solid: mp 187-190° C. ES-HRMS m/e calcd for C25H26ClN3O5 (M+Na) 506.1459, found 506.1455.

後処理

  1. customThe ethanol was removed under reduced pressure
  2. additionthe residue was diluted with water (30 mL)
  3. washThe aqueous solution was washed with diethyl ether (30 mL)
  4. customto remove any neutral impurities
  5. extractionthe product was extracted into ethyl acetate (2×35 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 of the filtrate

出典と根拠

ORDレコード
ord-4705880e4797414694e5885250fb4897
出典データセット
uspto-grants-2002_04
特許番号
US06380387B1

反応ノート

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