Monobasic potassium phosphate → (S)-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)ethyl)-quinoline-2-carboxylic acid

HRID 2044896ノート

反応式

HRID 2044896 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[C:8]([C@@H:14]([N:16]1[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]1=[O:26])[CH3:15])=[CH:7]2.[OH:27]P([O-])(O)=O.[K+].Cl([O-])=O.[Na+]>CC(=CC)C.CC(O)(C)C.C(Cl)Cl.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([OH:27])=[O:13])[C:8]([C@@H:14]([N:16]1[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]1=[O:26])[CH3:15])=[CH:7]2

参加物

10

反応物 3

HCID 516951Monobasic potassium phosphate2 回HCID 23668197Sodium Chlorite2 回HCID 57707962HCID 57707962、化合物

生成物 1

HCID 57707755(S)-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)ethyl)-quinoline-2-carboxylic acid

試薬・触媒・溶媒 6

HCID 311Citric Acid溶媒HCID 962Water溶媒3 回HCID 6344Dichloromethane溶媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒HCID 105532-Methyl-2-butene溶媒

実験手順

To a stirred solution of (S)-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)ethyl)-quinoline-2-carbaldehyde (110 mg, 0.30 mmol) and potassium phosphate monobasic (41.0 mg, 0.30 mmol) in 2-methyl-2-butene (2 mL), tBuOH (2 mL), DCM (1.0 mL) and water (2.0 mL) was added sodium chlorite (27.3 mg, 0.30 mmol) in water (2.0 mL). The reaction was stirred at room temperature. for 2 hours and then it was treated with additional potassium phosphate monobasic (41.0 mg, 0.30 mmol) and sodium chlorite (27.3 mg, 0.30 mmol) in water (2.0 mL). The reaction was stirred for 2 hours and then it was diluted with 1.0 M citric acid (40 mL) and ethyl acetate (60 mL). The separated aqueous layer was extracted withy ethyl acetate (2×60 mL) and the combined organic layers were washed with brine (40 mL), dried (MgSO4), filtered and evaporated in vacuo to give (S)-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)ethyl)quinoline-2-carboxylic acid. 1H NMR (400 MHz, CDCl3) δ ppm 8.62 (1H, s), 7.72-7.84 (6H, m), 7.65 (1H, dd, J=5.3, 2.9 Hz), 6.80 (1H, q, J=7.0 Hz), 1.96 (3H, d, J=7.0 Hz). Mass Spectrum (ESI) m/e=381.0 (M+1).

後処理

  1. stirringThe reaction was stirred for 2 hours
  2. extractionThe separated aqueous layer was extracted withy ethyl acetate (2×60 mL)
  3. washthe combined organic layers were washed with brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-cf9b36af7ea94031ad637f726bed50c4
出典データセット
uspto-grants-2013_11
特許番号
US08586739B2

反応ノート

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