Hydrochloric Acid → HCID 57557963, compound

HRID 1162928Notes

Reaction equation

HRID 1162928 reaction equation
CC1(C)[O:31][C@@H:5]2[CH2:6][N:7]([C:10]3[CH:19]=[C:18]4[C:13]([CH:14]=[C:15]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=5[C:27]([F:30])([F:29])[F:28])[NH:16][C:17]4=[O:20])=[CH:12][CH:11]=3)[C:8](=[O:9])[C@@H:4]2[O:3]1.Cl.[OH-].[Na+]>C1COCC1>[OH:3][C@@H:4]1[C@H:5]([OH:31])[CH2:6][N:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[C:15]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([F:29])([F:28])[F:30])[NH:16][C:17]3=[O:20])=[CH:12][CH:11]=2)[C:8]1=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57558093HCID 57558093, compound

Product 1

HCID 57557963HCID 57557963, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The 7-((3aR,6aR)-2,2-dimethyl-4-oxotetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (630 mg, 1.42 mmol) obtained in step C was dissolved in THF (15 ml). Thereafter, 1 N hydrochloric acid (8.1 ml, 8.1 mmol) was added to the solution. The obtained mixture was stirred for 4 hours, while gently heating. Thereafter, the reaction solution was cooled to 0° C., and a 1 N sodium hydroxide aqueous solution was added thereto until liquid property became pH 8. An organic layer was separated, and a water layer was extracted with ethyl acetate. The organic layer was mixed with the extract. The mixture was washed with water and a saturated saline solution, and was then dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol), so as to obtain 36.7 mg of 7-((3R,4R)-3,4-dihydroxy-2-oxopyrrolidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (7%).

Workup

  1. temperaturewhile gently heating
  2. customAn organic layer was separated
  3. extractiona water layer was extracted with ethyl acetate
  4. additionThe organic layer was mixed with the extract
  5. washThe mixture was washed with water
  6. dry with materiala saturated saline solution, and was then dried over anhydrous sodium sulfate
  7. distillationThereafter, the solvent was distilled away under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol)

Sources & evidence

ORD record
ord-79c3b809942b47a4b7041d37b62a8587
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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