Hydrochloric Acid → 3-amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one

HRID 1887773

反応式

HRID 1887773 の反応式
[O:1]=[C:2]1[CH:11]([NH:12]C(=O)OC(C)(C)C)[CH2:10][C:9]2[C:4](=[C:5]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:26][C:27]1[CH:31]=[CH:30][S:29][CH:28]=1.Cl.C(=O)(O)[O-].[K+]>C(OCC)(=O)C.O>[NH2:12][CH:11]1[CH2:10][C:9]2[C:4](=[C:5]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:2]1=[O:1]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 516893Potassium BicarbonateHCID 59620385Tert-butyl 2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

生成物 1

HCID 596203303-amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
37.5 °C

実験手順

tert-Butyl 2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (5.0 g) was suspended in ethyl acetate (30 mL), and 4N hydrochloric acid in ethyl acetate (28.3 mL) was added thereto, followed by stirring at 35-40° C. for one hour. The reaction mixture was added to a solution of potassium bicarbonate (11.3 g) in water (20 mL), and the mixture was partitioned at 45° C. The aqueous layer was extracted with ethyl acetate twice, and the organic layers were combined. The combined organic layer was concentrated under reduced pressure until precipitates were formed. The concentrated residue was stirred at room temperature for 30 minutes, and the formed precipitates were recovered through filtration. The thus-obtained solid was washed with ethyl acetate, and then dried under reduced pressure, whereby the title compound (2.93 g) was yielded as crystals.

後処理

  1. customthe mixture was partitioned at 45° C
  2. extractionThe aqueous layer was extracted with ethyl acetate twice
  3. concentrationThe combined organic layer was concentrated under reduced pressure
  4. customuntil precipitates
  5. customwere formed
  6. stirringThe concentrated residue was stirred at room temperature for 30 minutes
  7. customthe formed precipitates
  8. filtrationwere recovered through filtration
  9. washThe thus-obtained solid was washed with ethyl acetate
  10. dry with materialdried under reduced pressure, whereby the title compound (2.93 g)
  11. customwas yielded as crystals

出典と根拠

ORDレコード
ord-4c629df802944c8593f41cf148b5593f
出典データセット
uspto-grants-2013_08
特許番号
US08501772B2

関連ノート

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