Hydrochloric Acid → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid

HRID 1516201ノート

反応式

HRID 1516201 の反応式
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[CH2:18]([C:13]1[C:12]([CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:22])=[O:2])=[CH:5][N:6]=2)=[C:16]([CH3:17])[O:15][N:14]=1)[CH2:19][CH2:20][CH3:21]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 665991586-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

生成物 1

HCID 665983356-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid収率 76%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (1.0 g, 3.3 mmol) in THF (6 mL) was added a solution of lithium hydroxide monohydrate (248 mg, 9.8 mmol) in water (6 mL) added and the resulting mixture stirred at room temperture for 5 h. The mixture was acidified to pH 4 with HCl (1 N, 4.5 mL) and the resulting mixture extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, heptane:ethyl acetate=1:0 to 0:1) afforded the title compound (654 mg, 76%) which was obtained as a white solid. MS: m/e=291.2 [M+H]+.

後処理

  1. additionadded
  2. extractionthe resulting mixture extracted with ethyl acetate
  3. washThe combined organic layers were then washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customPurification by chromatography (silica, heptane:ethyl acetate=1:0 to 0:1)

出典と根拠

ORDレコード
ord-939995ae604e4aa7868796ac42222327
出典データセット
uspto-grants-2012_07
特許番号
US08227461B2

反応ノート

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