2,4-Dichlorobenzoic Acid → HCID 57798315、化合物

HRID 2100303ノート

反応式

HRID 2100303 の反応式
[NH2:1][C@H:2]([C:4]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]1)[CH3:3].[Cl:21][C:22]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:23]=1[C:24](O)=[O:25].C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[Cl:21][C:22]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:23]=1[C:24]([NH:1][C@H:2]([C:4]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:5][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7]1)[CH3:3])=[O:25]

参加物

5

反応物 3

HCID 57872,4-Dichlorobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 57798316HCID 57798316、化合物

生成物 1

HCID 57798315HCID 57798315、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of tert-butyl 3-[(1S)-1-aminoethyl]-3-pyridin-2-ylazetidine-1-carboxylate (I-3, 1.35 g, 5.1 mmol) in CH2Cl2 (11 mL) was treated with 2,4-dichlorobenzoic acid (1.2 g, 6.1 mmol) EDCI (2.0 g, 10.2 mmol), and HOBt (690 mg, 5.1 mmol) and stirred at room temperature. After 18 h, the reaction was quenched with the addition of H2O (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried (Na2SO4), concentrated under reduced pressure, and purified by flash chromatography (120 g SiO2, 50-80% EtOAc/hexanes) to afford tert-butyl 3-{(1S)-1-[(2,4-dichlorobenzoyl)amino]ethyl}-3-pyridin-2-ylazetidine-1-carboxylate (I-4). Analytical LCMS: single peak (214 nm), 3.010 min. This material was used in subsequent reactions without further purification.

後処理

  1. customthe reaction was quenched with the addition of H2O (50 mL)
  2. extractionextracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash chromatography (120 g SiO2, 50-80% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-6eeb31e77790485fa9051aa9f0ff7f45
出典データセット
uspto-grants-2009_08
特許番号
US07572792B2

反応ノート

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