Acetic Acid → HCID 67428638, compound

HRID 1662087Notes

Reaction equation

HRID 1662087 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13](OS(C)(=O)=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:21].[OH-].[Na+].[C:24]([OH:27])(=[O:26])[CH3:25]>C(OCC)(=O)C>[C:24]([OH:27])(=[O:26])[CH3:25].[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@@H:13]([NH2:21])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 14798Sodium HydroxideHCID 14555474(S)-1-((Benzyloxy)carbonyl)pyrrolidin-3-yl methanesulfonate

Product 1

HCID 67428638HCID 67428638, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In an autoclave were charged 2.44 g of (S)-1-(benzyloxycarbonyl)-3-(methanesulfonyloxy)pyrrolidine (7.38 mmol), and 15.7 g of 40% by weight aqueous ammonia (50 equivalent), which was heated to 80° C. whereby an internal pressure of 8 barr was observed. After allowing the reaction for 16 hrs, the reaction mixture was cooled to room temperature, followed by addition of a 30% by weight aqueous sodium hydroxide solution to adjust the pH to 13, and then ammonia was removed by distillation under reduced pressure. The residue was extracted with 15 mL of ethyl acetate three times, and the organic layers were combined. After washing with 3 mL of a saturated brine, drying over anhydrous magnesium sulfate, and concentration under reduced pressure gave a yellow oily material. When 10 mL of ethyl acetate, and 354 mg of acetic acid (0.8 equivalent) were added sequentially thereto, a crystal was precipitated. After stirring at 5° C. for 30 min, the crystal was filtrated under reduced pressure, which was washed with 10 mL of ethyl acetate, and thereafter vacuum drying was carried out to give a white crystal of 1.1684 g (yield: 56%, purity: 100% by weight, optical purity: 100% e.e.)

Workup

  1. customthe reaction for 16 hrs
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customammonia was removed by distillation under reduced pressure
  4. extractionThe residue was extracted with 15 mL of ethyl acetate three times
  5. washAfter washing with 3 mL of a saturated brine
  6. dry with materialdrying over anhydrous magnesium sulfate, and concentration under reduced pressure
  7. customgave a yellow oily material
  8. customa crystal was precipitated
  9. filtrationthe crystal was filtrated under reduced pressure, which
  10. washwas washed with 10 mL of ethyl acetate
  11. customvacuum drying
  12. customto give a white crystal of 1.1684 g (yield: 56%, purity: 100% by weight, optical purity: 100% e.e.)

Sources & evidence

ORD record
ord-f40b4d63091447e08453b0c06c942b03
Source dataset
uspto-grants-2011_10
Patent number
US08030501B2

Reaction notes

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