Water → HCID 10232658、化合物

HRID 895929

反応式

HRID 895929 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]([NH:11][C@H:12]([C:33]([OH:35])=[O:34])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:32])[N:22]([CH3:31])[C:23]([CH3:30])=[CH:24][C:25]=2[C:26]([F:29])([F:28])[F:27])=[CH:16][CH:15]=1)=[O:10].C(=O)(O)[O-].[Na+].[C:41]([O:44][CH:45](Cl)[CH3:46])(=[O:43])[CH3:42].O>CN(C=O)C>[C:41]([O:44][CH:45]([O:34][C:33](=[O:35])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21](=[O:32])[N:22]([CH3:31])[C:23]([CH3:30])=[CH:24][C:25]=2[C:26]([F:28])([F:29])[F:27])=[CH:18][CH:19]=1)[NH:11][C:9]([C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])=[O:10])[CH3:46])(=[O:43])[CH3:42]

参加物

6

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 5218651-Chloroethyl acetateHCID 9806910RO-0505376

生成物 1

HCID 10232658HCID 10232658、化合物収率 65.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of N-[(2,6-dichlorophenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine (145 mg, 0.275 mmol) and sodium bicarbonate (185 mg, 2.2 mmol) in DMF (2 mL) was added 1-chloroethyl acetate (270 mg, 2.2 mmol) at room temperature. The mixture was stirred for 48 h at room temperature. Then, the reaction mixture was poured into water (30 mL) and was extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with brine solution (60 mL) and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration gave the crude product, which was purified by silica gel chromatography using a Biotage (40 s) column to afford 110 mg (65% yield) of N-[(2,6-dichlorophenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine 1-(acetoxy)ethyl ester as an amorphous white solid. ES-HRMS m/e calcd for C28H25Cl2F3N2O6 (M+Na) 635.0931. found 635.0932.

後処理

  1. extractionwas extracted with ethyl acetate (3×20 mL)
  2. washThe combined organic extracts were washed with brine solution (60 mL)
  3. dry with materialwere dried over anhydrous magnesium sulfate
  4. filtrationFiltration of the drying agent and concentration
  5. customgave the crude product, which
  6. customwas purified by silica gel chromatography
  7. customa Biotage (40 s) column

出典と根拠

ORDレコード
ord-4467d180a4034336b0e5a79256d06785
出典データセット
uspto-grants-2005_07
特許番号
US06916933B2

関連ノート

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