Ethylene Glycol → (S)-3-chloro-N-(4-hydroxy-1-(4-(1-methyl-2-(2-methyl-1,3-dioxolan-2-yl)-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamide

HRID 1436199

반응식

HRID 1436199 반응식
[C:1]([C:4]1[N:5]([CH3:34])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][C:21](=[O:33])[C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[C:24]([Cl:32])[CH:23]=3)[CH2:17][CH2:18][OH:19])=[CH:11][CH:10]=2)[N:8]=1)(=[O:3])[CH3:2].[CH2:35](O)[CH2:36][OH:37].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:32][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[O:28][CH:29]([CH3:30])[CH3:31])[C:21]([NH:20][C@H:16]([CH2:17][CH2:18][OH:19])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[N:8]=[C:4]([C:1]3([CH3:2])[O:37][CH2:36][CH2:35][O:3]3)[N:5]([CH3:34])[CH:6]=2)=[CH:10][CH:11]=1)=[O:33]

참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 57594136(S)-N-(1-(4-(2-acetyl-1-methyl-1H-imidazol-4-yl)phenyl)-4-hydroxybutan-2-yl)-3-chloro-4-isopropoxybenzamide

생성물 1

HCID 57594713(S)-3-chloro-N-(4-hydroxy-1-(4-(1-methyl-2-(2-methyl-1,3-dioxolan-2-yl)-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamide수율 16%

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
70 °C

실험 절차

150 mg (0.31 mmol) of (S)-N-(1-(4-(2-acetyl-1-methyl-1H-imidazol-4-yl)phenyl)-4-hydroxybutan-2-yl)-3-chloro-4-isopropoxybenzamide in 2 mL of benzene was treated with 34.6 uL (0.62 mmol) of ethane-1,2-diol and 59 mg (0.31 mmol) of p-toluenesulfonic acid monohydrate. The reaction was stirred at 70° C. for 2 h after which the solvents were evaporated and the residue purified via reverse phase HPLC (acetonitrile/water). 25.5 mg (16% yield) of 4 was obtained and characterized by LCMS and HNMR.

후처리

  1. customwere evaporated
  2. customthe residue purified via reverse phase HPLC (acetonitrile/water)

출처 및 근거

ORD 기록
ord-ffcab30a72144937a3d156aeefaad9e6
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618981B2

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