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

HRID 844888

반응식

HRID 844888 반응식
C[O:2][C:3](=[O:31])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:30])[N:22]([CH3:29])[C:23](=[O:28])[N:24]([CH3:27])[C:25]=2[CH3:26])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[OH-].[Na+]>C(O)C.O>[CH3:11][C:9]([CH3:12])([O:8][C:6]([NH:5][C@H:4]([C:3]([OH:31])=[O:2])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:30])[N:22]([CH3:29])[C:23](=[O:28])[N:24]([CH3:27])[C:25]=2[CH3:26])=[CH:16][CH:15]=1)=[O:7])[CH3:10]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 69337009Methyl (2S)-2-(tert-butoxycarbonylamino)-3-[4-(1,3,4-trimethyl-2,6-dioxo-pyrimidin 5-yl)phenyl]propanoate

생성물 1

HCID 69337268N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine수율 94%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a suspension of N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester (8.8 mmol, 3.79 g) in ethanol (20 mL) was added aqueous 1.0 N sodium hydroxide (17.57 mL) at room temperature. The mixture was stirred for 2 h at room temperature. Then, the mixture was diluted with water (50 ml) and the ethanol was removed under reduced pressure. The aqueous solution was washed with diethyl ether (100 mL) to remove any neutral impurities. The aqueous layer was acidified with 1.0 N HCl and the product was extracted into ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (200 mL) and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the filtrate afforded 3.44 g (94% yield) of N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine as a light brown foam solid. ES-HRMS m/e calcd for C21H27N3O6 (M+Na) 440.1792, found 440.1792.

후처리

  1. customthe ethanol was removed under reduced pressure
  2. washThe aqueous solution was washed with diethyl ether (100 mL)
  3. customto remove any neutral impurities
  4. extractionthe product was extracted into ethyl acetate (2×100 mL)
  5. washThe combined organic extracts were washed with brine solution (200 mL)
  6. dry with materialwere dried over anhydrous magnesium sulfate
  7. filtrationFiltration of the drying agent and concentration of the filtrate

출처 및 근거

ORD 기록
ord-2e387ae221e64a0ebae92e8200a3fd11
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380387B1

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