Hydrochloric Acid → (S)-2'-oxo-1',2',5,7-tetrahydrospiro(cyclopenta(b)pyridine-6,3'-pyrrolo(2,3-b)-bipyridine)-3-carboxylic acid

HRID 588978Notes

Reaction equation

HRID 588978 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:22][C:13]1=[N:14][CH:15]=[C:16]([C:18]([O:20]C)=[O:19])[CH:17]=[C:12]1[CH2:11]2.[OH-].[Na+].Cl>CO>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:22][C:13]1=[N:14][CH:15]=[C:16]([C:18]([OH:20])=[O:19])[CH:17]=[C:12]1[CH2:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69098169Brt3qrq73F

Product 1

HCID 68746980(S)-2'-oxo-1',2',5,7-tetrahydrospiro(cyclopenta(b)pyridine-6,3'-pyrrolo(2,3-b)-bipyridine)-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of methyl (6S)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxylate (30.0 g, 102 mmol) and aqueous 6 N sodium hydroxide solution (50.8 mL, 305 mmol) in MeOH (920 mL) was heated at reflux for 1 h. The mixture was allowed to cool to 23° C. before it was acidified to pH ˜6 with aqueous 1 N hydrochloric acid solution, resulting in a black precipitate which was removed by filtration. The filtrate was concentrated under reduced pressure to a volume of ˜100 mL and then partitioned between water (500 mL) and 2-methyltetrahydrofuran (2-MeTHF, 250 mL). The aqueous layer was extracted with 2-MeTHF (5×250 mL), and the combined organic layers were dried over sodium sulfate and concentrated to provide the title compound. MS: m/z=282.0 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customresulting in a black precipitate which
  4. customwas removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure to a volume of ˜100 mL
  6. custompartitioned between water (500 mL) and 2-methyltetrahydrofuran (2-MeTHF, 250 mL)
  7. extractionThe aqueous layer was extracted with 2-MeTHF (5×250 mL)
  8. dry with materialthe combined organic layers were dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-230cc40c842f44a0b5f77be32efc05d0
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

Loading…