Trimethylsilyl iodide → O-Demethyl-N-deacetyl apremilast

HRID 532114노트

반응식

HRID 532114 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:29])[N:5]([C@@H:12]([C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[C:20]([O:26][CH2:27][CH3:28])[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]2=[O:11].I[Si](C)(C)C>C(Cl)Cl.[Cl-].[Na+].O>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:29])[N:5]([C@@H:12]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:26][CH2:27][CH3:28])[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]2=[O:11]

참가 물질

5

반응물 2

HCID 85247Trimethylsilyl iodideHCID 66718706APST-ZA

생성물 1

HCID 57524404O-Demethyl-N-deacetyl apremilast

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

To a stirred solution of (S)-4-amino-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-isoindole-1,3-dione (1 mmol) in anhydrous CH2Cl2 (20 mL), is added iodotrimethylsilane (6 mmol). The mixture is stirred at room temperature for 24 hours. The reaction mixture is diluted with brine and is extracted with CH2Cl1). The solvent is removed in vacuo to afford crude (S)-4-amino-2-[1-(3-ethoxy-4-hydroxy-phenyl)-2-methanesulfonyl-ethyl]-isoindole-1,3-dione. The product is purified by recrystallization.

후처리

  1. extractionis extracted with CH2Cl1)
  2. customThe solvent is removed in vacuo

출처 및 근거

ORD 기록
ord-0be9bd57ba004d15a4598bb9b0568678
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853175B2

반응 노트

불러오는 중…