反応式
[C:1]([O-:4])([O-])=[O:2].[K+].[K+].Br[C:8]1([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:18]>O1CCOCC1>[Cl:17][C:13]1[CH:12]=[C:11]2[C:16]([C:8]([NH:10][CH:9]([CH2:8][CH:16]([CH3:11])[CH3:15])[C:1]([OH:4])=[O:2])([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:9](=[O:18])[NH:10]2)=[CH:15][CH:14]=1参加物
実験手順
To the aqueous solution K2CO3 (1.6 μL, 1N) was added (2S)-amino-4-methyl-pentanoic (106 mg, 0.81 mmol), then followed by the addition of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (200 mg, 0.54 mmol) in dioxane (5 mL). After the mixture was stirred at room temperature for 4 h, the reaction mixture was concentrated in vacuo. Water (10 mL) was added and the crude was acidified with HCl to PH=4. The mixture was extracted with ethyl acetate (3×10 mL). The combined organic layer was concentrated in vacuo. The residue was purified by chromatography (DCM: MeOH=80:1) to give 184 mg of rac-(2S)-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-4-methyl-pentanoic acid as a white solid. MS: 421 (M+H)+. H1-NMR (400 MHz, CDCl3) δ 10.04 (s, 1H), 7.12 (m, 5H), 6.93 (t, 1H), 6.76 (m, 2H), 3.32 (m, 1H), 3.16 (dd, 2H), 1.89 (m, 1H), 1.50 (m, 2H), 0.90 (dd, 6H).
後処理
- concentrationthe reaction mixture was concentrated in vacuo
- additionWater (10 mL) was added
- extractionThe mixture was extracted with ethyl acetate (3×10 mL)
- concentrationThe combined organic layer was concentrated in vacuo
- customThe residue was purified by chromatography (DCM: MeOH=80:1)
出典と根拠
- ORDレコード
- ord-a9df929726304935be259ec4f10d1ae7
- 出典データセット
- uspto-grants-2011_11
- 特許番号
- US08058269B2
関連ノート
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