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2-Aminothiazole → Rac-2-(3-chloro-4-methanesulfonyl-phenyl)-2-(cyclohex-2-enyloxy)-n-thiazol-2-yl-acetamide

HRID 1019214
ノート
印刷プレビュー

反応式

HRID 1019214 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH:19]=[CH:18]2)[C:13]([OH:15])=O)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[NH2:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH:19]=[CH:18]2)[C:13]([NH:23][C:24]2[S:25][CH:26]=[CH:27][N:28]=2)=[O:15])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 18172587Rac-(3-chloro-4-methanesulfonyl-phenyl)-(cyclohex-2-enyloxy)-acetic acid

生成物 1

HCID 12088826Rac-2-(3-chloro-4-methanesulfonyl-phenyl)-2-(cyclohex-2-enyloxy)-n-thiazol-2-yl-acetamide収率 63%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of rac-(3-chloro-4-methanesulfonyl-phenyl)-(cyclohex-2-enyloxy)-acetic acid (50 mg, 0.15 mmol) in dichloromethane (10 mL) at 25° C. was added 2-aminothiazole (22 mg, 0.22 mmol), BOP reagent (96.2 mg, 0.22 mmol) and triethylamine (0.06 mL, 0.44 mmol). The mixture was stirred at 25° C. for 16 h, then was diluted with water (10 mL) and extracted with dichloromethane (3×20 mL). The combined organic layers were washed with water (1×10 mL), 1N sodium hydroxide (1×10 mL), 1N hydrochloric acid (1×10 mL) and brine ( 1×10 mL), then were dried over sodium sulfate, filtered and evaporated under reduced pressure. The product was purified by chromatography (Biotage Flash 40S column, 60/40 hexanes/ethyl acetate) to furnish rac-2-(3-chloro-4-methanesulfonyl-phenyl)-2-(cyclohex-2-enyloxy)-N-thiazol-2-yl-acetamide (39 mg, 63% yield) as a glassy solid: EI-HRMS m/e calculated for C18H19N2O4S2Cl (M+) 426.0475, found 426.0479.

後処理

  1. extractionextracted with dichloromethane (3×20 mL)
  2. washThe combined organic layers were washed with water (1×10 mL), 1N sodium hydroxide (1×10 mL), 1N hydrochloric acid (1×10 mL) and brine ( 1×10 mL)
  3. dry with materialwere dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe product was purified by chromatography (Biotage Flash 40S column, 60/40 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-6366596dc9d74479bf577e6093864344
出典データセット
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06486184B2

反応ノート

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