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Ethanethiol → (S)-1-(4-(3-(ethylthio)-2-hydroxypropoxy)-3-methoxyphenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one

HRID 1044416
ノート
印刷プレビュー

反応式

HRID 1044416 の反応式
[CH2:1]([SH:3])[CH3:2].[OH-].[K+].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([N:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[CH:21][C:20]2=[O:35])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C@H:16]1[CH2:18][O:17]1>C1COCC1.CCOC(C)=O>[CH2:1]([S:3][CH2:18][C@@H:16]([OH:17])[CH2:15][O:14][C:13]1[CH:12]=[CH:11][C:10]([N:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:27][CH:26]=3)=[CH:21][C:20]2=[O:35])=[CH:9][C:8]=1[O:7][CH3:6])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6343EthanethiolHCID 14797Potassium HydroxideHCID 86660698(R)-1-(3-methoxy-4-(oxiran-2-ylmethoxy)phenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one

生成物 1

HCID 67134772(S)-1-(4-(3-(ethylthio)-2-hydroxypropoxy)-3-methoxyphenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one収率 76%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Ethanethiol (47.6 mg, 0.76 mmol) and 25% aq. potassium hydroxide (172 mg, 0.77 mmol) were added to a solution of (R)-1-(3-methoxy-4-(oxiran-2-ylmethoxy)phenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (32 mg, 0.08 mmol) Part A in THF (1.5 mL). The mixture was stirred overnight at RT. Diluted with EtOAc, washed with sat. NaHCO3, dried (Na2SO4), and concentrated. The residue was purified using ISCO flash chromatography (silica gel/hexanes/ethyl acetate 100:0 to 0:100 gradient) to afford the desired product (S)-1-(4-(3-(ethylthio)-2-hydroxypropoxy)-3-methoxyphenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one 15B (28 mg, 0.06 mmol, 76% yield) as a light yellow solid. LC/MS 480 (M+H)+, tR 0.97 min (method 5).

後処理

  1. washwashed with sat. NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified

出典と根拠

ORDレコード
ord-ec159efebc7b4afa8cc85a9cd19811f6
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08563583B2

反応ノート

読み込み中…

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