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

HRID 844849ノート

反応式

HRID 844849 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([CH2:13][CH2:14][O:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[OH-].[Na+]>C(O)C>[CH3:16][O:15][CH2:14][CH2:13][C:8]1([C:6]([NH:5][C@H:4]([C:3]([OH:35])=[O:2])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:25](=[O:34])[N:26]([CH3:33])[C:27](=[O:32])[N:28]([CH3:31])[C:29]=3[CH3:30])=[CH:20][CH:19]=2)=[O:7])[CH2:12][CH2:11][CH2:10][CH2:9]1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 69336589N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester

生成物 1

HCID 10116180N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine収率 94%

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-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester (0.273 mmol, 133 mg) in ethanol (3 mL) was added aqueous 1.0 N sodium hydroxide (1.5 mL) at room temperature. The mixture was heated to 40-45° C. and the resulting clear solution was stirred for 15 h. The ethanol was removed under reduced pressure and the residue was diluted with water (25 mL) and NaOH (3 mL, 1.0N) to dissolve the sodium salt. The aqueous solution was washed with diethyl ether (50 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 of the filtrate afforded 121 mg (94% yield) of N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine as an amorphous white solid. FAB-HRMS m/e calcd for C25H33N3O6 (M+H) 472.2448, found 472.2467.

後処理

  1. customThe ethanol was removed under reduced pressure
  2. additionthe residue was diluted with water (25 mL) and NaOH (3 mL, 1.0N)
  3. dissolutionto dissolve the sodium salt
  4. washThe aqueous solution was washed with diethyl ether (50 mL)
  5. customto remove any neutral impurities
  6. extractionthe product was extracted into ethyl acetate (2×25 mL)
  7. washThe combined organic extracts were washed with brine solution (50 mL)
  8. dry with materialwere dried over anhydrous magnesium sulfate
  9. filtrationFiltration of the drying agent and concentration of the filtrate

出典と根拠

ORDレコード
ord-869e31d829644db7a2e7688a55207aa9
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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