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

HRID 588971노트

반응식

HRID 588971 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 6395Methanesulfonic Acid용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-effc892788794a3bb45f771b77a2db68
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227973B2

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