Lithium Hydroxide → 2-[2-(Benzhydrylidene-amino)-3-fluoropyridin-4-ylmethyl]-3-oxobutanoic acid ethyl ester

HRID 599860ノート

反応式

HRID 599860 の反応式
[C:1](=[N:14][C:15]1[C:20]([F:21])=[C:19]([CH2:22]O)[CH:18]=[CH:17][N:16]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.CC(C)([O-])C.[Li+].[CH2:35]([O:37][C:38](=[O:43])[CH2:39][C:40]([CH3:42])=[O:41])[CH3:36].[Na+].[I-].[Li+].[OH-]>C1COCC1.C(OCC)(=O)C>[CH2:35]([O:37][C:38](=[O:43])[CH:39]([CH2:22][C:19]1[CH:18]=[CH:17][N:16]=[C:15]([N:14]=[C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:20]=1[F:21])[C:40](=[O:41])[CH3:42])[CH3:36]

参加物

9

反応物 6

HCID 3939Lithium HydroxideHCID 5238Sodium IodideHCID 8868Ethyl AcetoacetateHCID 31297Methanesulfonyl chlorideHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)2 回HCID 59139234[2-(Benzhydrylidene-amino)-3-fluoropyridin-4-yl]-methanol

生成物 1

HCID 591392862-[2-(Benzhydrylidene-amino)-3-fluoropyridin-4-ylmethyl]-3-oxobutanoic acid ethyl ester収率 102.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A mixture of [2-(benzhydrylidene-amino)-3-fluoropyridin-4-yl]-methanol (compound 8c-4) (5 g, 16.3 mmol), methanesulfonyl chloride (1.52 mL, 19.6 mmol) and lithium tert-butoxide (in THF) (18 mL, 18 mmol) in THF (40 mL) was stirred at 0° C. for 1 hour. The mixture was added to a solution of acetoacetic acid ethyl ester (4.16 mL, 32.7 mmol), lithium tert-butoxide (in THF) (19.6 mL, 19.6 mmol) and NaI (2.5 g, 16.3 mmol) in THF (18 mL). The solution was stirred at 50° C. for 3 hours, 0.2N LiOH (in water) and ethyl acetate were added thereto, and the solution was washed with 0.2N LiOH (in water) and saturated saline. After drying over anhydrous magnesium sulfate, the solvent was distilled away under reduced pressure to yield the title compound (6.98 g, quant.).

後処理

  1. stirringThe solution was stirred at 50° C. for 3 hours
  2. washthe solution was washed with 0.2N LiOH (in water) and saturated saline
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure

出典と根拠

ORDレコード
ord-6637341028af40e1bd4471cd504d355d
出典データセット
uspto-grants-2011_03
特許番号
US07897792B2

反応ノート

読み込み中…