Hydrochloric Acid → HCID 131734541, compound

HRID 592091Notes

Reaction equation

HRID 592091 reaction equation
[K].[CH3:2][O:3][CH2:4][C:5]([CH:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C:8]1=[O:22])=O.Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:36][C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=1.C(=O)(O)[O-].[Na+]>C1CCCCC1.C1(C)C=CC=CC=1>[F:36][C:37]1[CH:43]=[CH:42][C:40]([NH:41][C:5](=[C:7]2[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C:8]2=[O:22])[CH2:4][O:3][CH3:2])=[CH:39][CH:38]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 97314-FluoroanilineHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 117841208HCID 117841208, compound

Product 1

HCID 131734541HCID 131734541, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8078CyclohexaneSolvent

Conditions

Temperature
25 °C

Procedure

Into a 100 mL eggplant-shaped flask were added benzyl 3-(2-methoxyacetyl)-2-oxopyrrolidine-1-carboxylate potassium salt (2.93 g) [mw. 329.39, 8.9 mmol], 1 mol/L hydrochloric acid (16 mL) [16 mmol] and toluene (32 mL), and the mixture was stirred for 20 min. After partitioning, the organic layer was concentrated under reduced pressure, and to the concentrate were added toluene (12 mL), cyclohexane (36 mL), p-toluenesulfonic acid monohydrate (18.0 mg) [mw. 190.22, 0.09 mmol] and p-fluoroaniline (0.99 g) [mw. 111.12, 8.9 mmol]. Dean-Stark trap was set, and the mixture was subjected to dehydration reflux for 2 hr. After cooling to 25° C., 5 w/w % aqueous sodium bicarbonate solution (10 mL) was added and the mixture was partitioned. The organic layer was washed with water (10 mL), dried over magnesium sulfate and, after filtration, concentrated under reduced pressure. To the concentrate were added toluene (20 mL) and 10 w/w % aqueous citric acid solution, and the mixture was stirred and partitioned. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. Yellow candy-like product, 2.56 g, yield 74.8%. 1H-NMR (500 MHz, CDCl3, TMS) δ 2.77 (s, 1H), 3.31 (s, 3H), 3.81 (t, J=5.0 Hz, 2H), 3.96 (s, 2H), 5.30 (s, 2H), 6.90-7.12 (m, 5H), 7.22-7.49 (m, 5H), 10.44 (s, 1H).

Workup

  1. customAfter partitioning
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. temperaturereflux for 2 hr
  4. additionwas added
  5. customthe mixture was partitioned
  6. washThe organic layer was washed with water (10 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationafter filtration
  9. concentrationconcentrated under reduced pressure
  10. additionTo the concentrate were added toluene (20 mL) and 10 w/w % aqueous citric acid solution
  11. stirringthe mixture was stirred
  12. custompartitioned
  13. dry with materialThe organic layer was dried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab966869f47c4d6b93fe13a76a6e886a
Source dataset
uspto-grants-2016_01
Patent number
US09238667B2

Reaction notes

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