Sodium Hydroxide → 4-[(S)-3-tert-Butoxycarbonylaminopyrrolidin-1-yl]-3-chloro-2-cyclopropylamino-5-fluoro-benzoic acid

HRID 10296노트

반응식

HRID 10296 반응식
C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)=[C:7]([Cl:25])[C:6]=1[NH:26][CH:27]1[CH2:29][CH2:28]1)C.[OH-].[Na+]>CO.O1CCCC1.C(OCC)(=O)C>[C:21]([O:20][C:18]([NH:17][C@H:14]1[CH2:15][CH2:16][N:12]([C:8]2[C:9]([F:11])=[CH:10][C:5]([C:4]([OH:30])=[O:3])=[C:6]([NH:26][CH:27]3[CH2:28][CH2:29]3)[C:7]=2[Cl:25])[CH2:13]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 578326504-((s)-3-Tert-butoxycarbonylaminopyrrolidin-1-yl)-3-chloro-2-cyclopropylamino-5-fluorobenzoic acid ethyl ester

생성물 1

HCID 586818934-[(S)-3-tert-Butoxycarbonylaminopyrrolidin-1-yl]-3-chloro-2-cyclopropylamino-5-fluoro-benzoic acid

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a solution of 4-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-3-chloro-2-cyclopropylamino-5-fluorobenzoic acid ethyl ester (Example 3c, 2.90 g, 6.56 mmol) in methanol (30 mL) and tetrahydrofuran (30 mL) is added a 1N solution of sodium hydroxide (50 mL). The reaction mixture is stirred at 80° C. for 20 hours, cooled to room temperature, and diluted with ethyl acetate. The organic layer is washed with 1N hydrochloric acid, water, and brine. The organic layer is dried over MgSO4, filtered, and filtrate concentrated to the title compound as a solid (2.74 g). MS CI: m/z 414 (MH+).

후처리

  1. temperaturecooled to room temperature
  2. washThe organic layer is washed with 1N hydrochloric acid, water, and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationfiltrate concentrated to the title compound as a solid (2.74 g)

출처 및 근거

ORD 기록
ord-ad384940417e4d18b0bae0170e802d31
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094780B1

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