N,N-二异丙基乙胺 → (s)-Tert-butyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamoyl)pyrrolidine-1-carboxylate

HRID 75088

反应方程式

HRID 75088 反应方程式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[B:8]1[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:12])([CH3:11])[O:9]1.[C:17]([N:24]1[CH2:31][CH2:30][CH2:29][C@H:25]1[C:26](O)=[O:27])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:12][C:10]1([CH3:11])[C:13]([CH3:15])([CH3:14])[O:16][B:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:26]([C@@H:25]2[CH2:29][CH2:30][CH2:31][N:24]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:27])[O:9]1

参与物

6

反应物 4

HCID 81531N,N-二异丙基乙胺HCID 85083BOC-L-脯氨酸HCID 27239391-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐HCID 27346522-氨基苯硼酸频哪醇酯

产物 1

HCID 66982669(s)-Tert-butyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamoyl)pyrrolidine-1-carboxylate

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
60 °C

实验过程

To 2-aminophenylboronic acid pinacol ester a (3.0 g, 0.014 mol) and N-Boc-L-proline b (3.0 g, 0.014 mol) in N,N-dimethylformamide (15 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.6 g, 0.014 mol), 1-hydrozybenzotriazole (1.9 g, 0.014 mol), and then N,N-diisopropylethylamine (2.4 mL, 0.014 mol). The reaction was heated to 60° C., stirred several days, cooled to room temperature, and then quenched by the addition of a saturated aqueous solution of sodium bicarbonate. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over MgSO4, filtered, and concentrated. The crude residue was purified by ISCO chromatography (80 g column, 0 to 80% EtOAc/Hexanes) to give (S)-tert-butyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamoyl)pyrrolidine-1-carboxylate c (2.87 g, 49%).

后处理

  1. temperaturecooled to room temperature
  2. customquenched by the addition of a saturated aqueous solution of sodium bicarbonate
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by ISCO chromatography (80 g column, 0 to 80% EtOAc/Hexanes)

来源与证据

ORD记录
ord-714b6f05ea764ba7911f350ae3155c03
来源数据集
uspto-grants-2014_09
专利号
US08835393B2

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