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

HRID 1355108노트

반응식

HRID 1355108 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-78933154fc8347cdaaa91b092c0a6d9b
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223868B2

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