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

HRID 588971Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-effc892788794a3bb45f771b77a2db68
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227973B2

Reaction notes

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