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

HRID 2070129ノート

反応式

HRID 2070129 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.[OH-].[Na+]>C(O)C>[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

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 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 1

HCID 702Ethanol溶媒

反応条件

温度
60 °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 (399 g) was suspended in ethanol (2 L), and concentrated hydrochloric acid (555 mL) was added to the suspension, followed by stirring at 60° C. for 30 minutes. The reaction mixture was neutralized with 25% aqueous sodium hydroxide solution under cooling on ice. The resultant mixture was partitioned between chloroform and water, and the aqueous layer was extracted with chloroform. The organic layers were combined, and the combined organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, whereby the title compound (418 g) in a crude form was yielded, which was employed in the subsequent reaction step without performing further purification.

後処理

  1. temperatureunder cooling on ice
  2. customThe resultant mixture was partitioned between chloroform and water
  3. extractionthe aqueous layer was extracted with chloroform
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure, whereby the title compound (418 g) in a crude form
  6. customwas yielded
  7. customwhich was employed in the subsequent reaction step
  8. custompurification

出典と根拠

ORDレコード
ord-5d50a66e06604a60bfd1055d6f69ce1e
出典データセット
uspto-grants-2012_10
特許番号
US08299255B2

反応ノート

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