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

HRID 844858노트

반응식

HRID 844858 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4705880e4797414694e5885250fb4897
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380387B1

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