Hydrochloric Acid → HCID 86618516, compound

HRID 1010569Notes

Reaction equation

HRID 1010569 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]1[C@@H:15]([CH3:16])[CH2:14][N:13]([C:17]2[C:27]([F:28])=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[C:19]([F:29])[C:18]=2[CH3:30])[CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl>C(O)C>[C:3]([O:7][C:8]([NH:10][C@H:11]1[C@@H:15]([CH3:16])[CH2:14][N:13]([C:17]2[C:27]([F:28])=[CH:26][C:20]([C:21]([OH:23])=[O:22])=[C:19]([F:29])[C:18]=2[CH3:30])[CH2:12]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86618515HCID 86618515, compound

Product 1

HCID 86618516HCID 86618516, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 1 mol/L aqueous sodium hydroxide solution (15 mL, 15 mmol) was added under cooling with ice to a solution of ethyl 4-[(3S,4S)-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidin-1-yl]-2,5-difluoro-3-methylbenzoate (2.51 g, 6.30 mmol) in ethanol (20 mL), followed by stirring at room temperature for 20 hours. The resultant mixture was neutralized with 1 mol/L hydrochloric acid under cooling with ice, and ethanol was removed under reduced pressure. Subsequently, 1 mol/L hydrochloric acid was added to the residue, and the mixture was extracted with ethyl acetate (200 mL×2), followed by drying over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and dried under reduced pressure (solvent), to thereby yield the title compound as a yellow oily substance (2.20 g, quantitative amount). The product was employed, without further purification, in the subsequent step.

Workup

  1. customwas removed under reduced pressure
  2. additionSubsequently, 1 mol/L hydrochloric acid was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate (200 mL×2)
  4. dry with materialby drying over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customdried under reduced pressure (solvent)

Sources & evidence

ORD record
ord-ca95e499ec314d13b05ab02888fb1307
Source dataset
uspto-grants-2011_07
Patent number
US07977327B2

Reaction notes

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