Hydrochloric Acid → (R)-2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-carboxylic acid

HRID 334848ノート

反応式

HRID 334848 の反応式
C([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C@@:7]2([CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:22]([O:24]C)=[O:23])[CH:19]=3)[CH2:14]2)[C:6]1=[O:26])(C)(C)C.[OH-].[Na+].Cl>CS(O)(=O)=O.O>[O:26]=[C:6]1[NH:5][C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C@:7]21[CH2:21][C:20]1[C:15](=[CH:16][CH:17]=[C:18]([C:22]([OH:24])=[O:23])[CH:19]=1)[CH2:14]2

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69965262(R)-methyl 1'-tert-butyl-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-carboxylate

生成物 1

HCID 69965156(R)-2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6395Methanesulfonic Acid溶媒

反応条件

温度
90 °C

実験手順

A solution of (R)-methyl 1′-tert-butyl-2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridine]-5-carboxylate (53 g, 151 mmol) in methanesulfonic acid (196 mL) was heated at 90° C. for 1 h. Water (100 mL) was added and the solution was stirred for an additional 3 h at 90° C. The acidic mixture was cooled to 0° C., diluted with water (1 L), and basified to pH 14 with 50% aqueous NaOH solution. The basic mixture was then acidified to pH 3 by careful addition of concentrated aqueous HCl solution. The solids were collected by filtration and dried under nitrogen atmosphere to give the title compound which was used without further purification. MS: m/z=281.1 (M+1).

後処理

  1. temperatureThe acidic mixture was cooled to 0° C.
  2. filtrationThe solids were collected by filtration
  3. customdried under nitrogen atmosphere

出典と根拠

ORDレコード
ord-5cc45a6890994ef78f515fd7e9dfee25
出典データセット
uspto-grants-2014_11
特許番号
US08883807B2

反応ノート

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