Ammonium Chloride → 2-(3-amino-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide

HRID 1355108ノート

反応式

HRID 1355108 の反応式
[CH:1]1([CH2:6][CH:7]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18]([N+:26]([O-])=O)[CH:17]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+]>CO.O.[Zn]>[NH2:26][C:18]1[CH:17]=[C:16]([CH:7]([CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH:21]=[CH:20][C:19]=1[S:22]([CH3:25])(=[O:23])=[O:24]

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 120889203-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-N-thiazol-2-yl-propionamide

生成物 1

HCID 223151332-(3-amino-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide収率 43.1%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

A solution of 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-N-thiazol-2-yl-propionamide (prepared as in Example 67, 100 mg, 0.236 mmol) in methanol (2 mL) was treated with a solution of ammonium chloride (27 mg, 0.500 mmol) in water (200 μL). The reaction mixture was then treated with zinc dust (151 mg, 2.31 mmol). The reaction mixture was heated under reflux for 2 h. The reaction mixture was allowed to cool to 25° C. and then filtered through a pad of celite. The celite pad was washed well with methanol. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 1/1 hexanes/ethyl acetate) afforded 2-(3-amino-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (40 mg, 43%) as a white solid: mp 207–209° C.; EI-HRMS m/e calcd for C18H23N3O3S2 (M+) 393.1181, found 393.1180.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. filtrationfiltered through a pad of celite
  4. washThe celite pad was washed well with methanol
  5. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-78933154fc8347cdaaa91b092c0a6d9b
出典データセット
uspto-grants-2007_05
特許番号
US07223868B2

反応ノート

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