Ethyl Acetate → HCID 86648339, compound

HRID 1961581Notes

Reaction equation

HRID 1961581 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([NH:14][CH2:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[C:23]#[N:24])=[O:17])([CH3:13])[CH2:12][CH:7]2[CH2:6]1)=[O:4].O.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([OH:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1.C(OCC)(=O)C>ClCCl>[C:27]1([CH3:37])[CH:28]=[CH:29][C:30]([S:33]([OH:36])(=[O:34])=[O:35])=[CH:31][CH:32]=1.[CH3:25][N:2]([CH3:1])[C:3]([N:5]1[CH2:6][CH:7]2[CH2:12][C:11]([NH:14][CH2:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[C:23]#[N:24])=[O:17])([CH3:13])[CH2:10][CH:8]2[CH2:9]1)=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 68775608HCID 68775608, compound

Product 1

HCID 86648339HCID 86648339, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[2-((S)-2-Cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 11d (20 mg, 0.057 mmol) and p-toluenesulfonic acid monohydrate (12 mg, 0.063 mmol) were dissolved in 2 mL of dichloromethane with stirring upon cooling by an ice-water bath. The reaction mixture was stirred for 10 minutes at the same temperature and the ice-water bath was removed. The mixture was concentrated under reduced pressure to obtain an oil. The mixture was treated with 5 mL of ethyl acetate with stirring to produce a white precipitate. The mixture was filtered under reduced pressure to obtain the title compound 5-[2-((S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide p-toluenesulfonate 11 (0.026 g, yield 86.8%) as a white solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. stirringThe reaction mixture was stirred for 10 minutes at the same temperature
  3. customthe ice-water bath was removed
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customto obtain an oil
  6. stirringwith stirring
  7. customto produce a white precipitate
  8. filtrationThe mixture was filtered under reduced pressure

Sources & evidence

ORD record
ord-58b71bd13ac94a1abcffa3a5b3d764d8
Source dataset
uspto-grants-2013_04
Patent number
US08415349B2

Reaction notes

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