Hydrochloric Acid → 3-Mercapto-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine

HRID 1583539Notes

Reaction equation

HRID 1583539 reaction equation
C([S:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10](=[N:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[O:14])[CH3:11])[CH2:6]1)(=O)C.C[O-].[Na+].Cl>CO>[SH:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10](=[N:12][C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)=[O:14])[CH3:11])[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 540371453-Acetylthio-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine

Product 1

HCID 534008923-Mercapto-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidineYield 75.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 30 g of 3-acetylthio-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine in 1000 ml of methanol was cooled to -10° C. A solution of sodium methoxide in methanol (prepared from 1.8 g of sodium) was then added dropwise to the cooled solution, after which the mixture was stirred for 30 minutes, whilst gradually raising the temperature to 0° C. At the end of this time, 65.2 ml of 10% w/v hydrochloric acid were added to the reaction mixture, which was then concentrated to half of its original volume by evaporation in vacuo. A saturated aqueous solution of sodium chloride was added to the concentrate and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried, after which the solvent was distilled off under reduced pressure. The residue was purified by chromatography through a column of silica gel, eluted with a 2:1 by volume mixture of benzene and ethyl acetate, to give 20 g of the title compound.

Workup

  1. additionwere added to the reaction mixture, which
  2. concentrationwas then concentrated to half of its original volume by evaporation in vacuo
  3. additionA saturated aqueous solution of sodium chloride was added to the
  4. concentrationconcentrate
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. customdried
  8. distillationafter which the solvent was distilled off under reduced pressure
  9. customThe residue was purified by chromatography through a column of silica gel
  10. washeluted with a 2:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-b688f42ee3874320bf9c622be60a049a
Source dataset
uspto-grants-1985_11
Patent number
US04552873

Reaction notes

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