Hydrochloric Acid → HCID 131734544, compound

HRID 592094Notes

Reaction equation

HRID 592094 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.[CH3:36][O:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1.C(=O)(O)[O-].[Na+]>C1CCCCC1.C1(C)C=CC=CC=1>[CH3:36][O:37][C:38]1[CH:44]=[CH:43][C:41]([NH:42][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:40][CH:39]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 117841208HCID 117841208, compound

Product 1

HCID 131734544HCID 131734544, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 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 (4.94 g) [mw. 329.39, 15.0 mmol], 1 mol/L hydrochloric acid (25 mL) [25 mmol] and toluene (50 mL), and the mixture was stirred for 20 min. After partitioning, the organic layer was dried over magnesium sulfate. After filtration, to the mother liquor were added cyclohexane (30 mL), p-toluenesulfonic acid monohydrate (29.0 mg) [mw. 190.22, 0.15 mmol] and p-methoxyaniline (1.85 g) [mw. 123.15, 15.0 mmol]. Dean-Stark trap was set, and the mixture was subjected to dehydration reflux for 30 min. After cooling to 25° C., 5 w/w % aqueous sodium bicarbonate solution (25 mL) was added to allow for partitioning. The organic layer was washed with 5 w/w % aqueous acetic acid solution (25 mL), further washed with 5 w/w % aqueous sodium bicarbonate solution (25 mL), dried over magnesium sulfate, filtered, concentrated under reduced pressure and purified by basic silica gel column chromatography (silica gel amount: 100 g, eluent:toluene, Rf=0.2). The effective section was concentrated under reduced pressure. Yellow candy-like product, 3.63 g, yield 61.0%, 1H-NMR (500 MHz, CDCl3, TMS) δ2.74-2.77 (m, 2H), 3.29 (s, 3H), 3.75-3.80 (m, 5H), 3.95 (s, 2H), 5.28 (s, 2H), 6.83 (d, J=8.8 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 7.25-7.38 (m, 3H), 7.43 (d, J=7.2 Hz, 2H), 10.41 (s, 1H).

Workup

  1. customAfter partitioning
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationAfter filtration
  4. temperaturereflux for 30 min
  5. additionwas added
  6. customfor partitioning
  7. washThe organic layer was washed with 5 w/w % aqueous acetic acid solution (25 mL)
  8. washfurther washed with 5 w/w % aqueous sodium bicarbonate solution (25 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. custompurified by basic silica gel column chromatography (silica gel amount: 100 g, eluent:toluene, Rf=0.2)
  13. concentrationThe effective section was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8e932c6610944a22a1982ef0714e55be
Source dataset
uspto-grants-2016_01
Patent number
US09238667B2

Reaction notes

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