Sodium Hydroxide → HCID 56591700, 화합물

HRID 2047705노트

반응식

HRID 2047705 반응식
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[N:11]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH:10]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)[CH2:9][C:8]([CH2:29][CH3:30])([CH3:28])[C:7]=2[N:6]=1)=[O:4].[OH-].[Na+]>O1CCCC1.CO.O>[Cl:27][C:22]1[CH:21]=[C:20]([CH:10]2[CH2:9][C:8]([CH2:29][CH3:30])([CH3:28])[C:7]3[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=[CH:13][C:12]=3[N:11]2[CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])[CH:25]=[CH:24][C:23]=1[F:26]

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 665877056-(3-Chloro-4-fluoro-phenyl)-8-ethyl-8-methyl-5-(3-methyl-butyl)-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid methyl ester

생성물 1

HCID 56591700HCID 56591700, 화합물수율 35.8%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-(3-chloro-4-fluoro-phenyl)-8-ethyl-8-methyl-5-(3-methyl-butyl)-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid methyl ester (100 mg, 0.2 mmol) in tetrahydrofuran (2 mL) and methanol (2 mL) was added 3 N sodium hydroxide (1 mL). The reaction mixture was stirred at room temperature for 16 hours, and then diluted with water (10 mL), extracted with diethyl ether (20 mL). The organic layer was discarded. The aqueous layer was acidified with concentrated hydrochloric acid to pH 4 and extracted with ethyl acetate (40 mL×3), and the combined organics were dried over anhydrous Na2SO4. The solvent was removed in vacuo and purified by preparative HPLC to afford 6-(3-chloro-4-fluoro-phenyl)-8-ethyl-8-methyl-5-(3-methyl-butyl)-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid (30 mg, 31.3%) as a yellow oil. MS (ESI+) [(M+H)+] 419.1.

후처리

  1. extractionextracted with diethyl ether (20 mL)
  2. extractionextracted with ethyl acetate (40 mL×3)
  3. dry with materialthe combined organics were dried over anhydrous Na2SO4
  4. customThe solvent was removed in vacuo
  5. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-e751588415974bbaaa8386904d2f9251
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592594B2

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