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

HRID 844888ノート

反応式

HRID 844888 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2e387ae221e64a0ebae92e8200a3fd11
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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