Sodium Hydroxide → HCID 56591700、化合物

HRID 2047705ノート

反応式

HRID 2047705 の反応式
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]

参加物

6

反応物 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

生成物 1

HCID 56591700HCID 56591700、化合物収率 35.8%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e751588415974bbaaa8386904d2f9251
出典データセット
uspto-grants-2013_11
特許番号
US08592594B2

反応ノート

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