Trifluoroacetic acid → (1-{1-[6-(3,4-Difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester

HRID 1965180Notes

Reaction equation

HRID 1965180 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[CH:10]2[N:22]([C:25](=[O:48])[CH:26]([NH:31][C:32](=[O:47])[CH:33]([N:35]([C:37]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:38])[CH3:36])[CH3:34])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:24][CH:9]12)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:40]([O:39][C:37](=[O:38])[N:35]([CH:33]([C:32](=[O:47])[NH:31][CH:26]([C:25]([N:22]1[CH2:23][CH2:24][CH:9]2[NH:8][CH2:12][CH:11]([O:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=3)[CH:10]12)=[O:48])[C:27]([CH3:28])([CH3:30])[CH3:29])[CH3:34])[CH3:36])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 676065094-{2-[2-(Benzyloxycarbonyl-methyl-amino)-propionylamino]-3,3-dimethyl-butyryl}-3-(3,4-difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

Product 1

HCID 67606709(1-{1-[6-(3,4-Difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl esterYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The Boc-containing compound 34 (2.0 g, 3.0 mmol) was dissolved in DCM (30 mL) and cooled to 0° C. TFA (10 mL) was added and the reaction mixture was slowly warmed to ambient temperature. After 2 h, the reaction mixture was concentrated in vacuo and the crude residue was dissolved in EtOAc and washed successively with saturated aqueous NaHCO3 and brine. The organic extract was dried over anhydrous Na2SO4, filtered, and concentrated to afford 1.75 g of compound 35 as a white solid. Mass spectrum, m/z [573.1] (M+H)+.

Workup

  1. temperaturethe reaction mixture was slowly warmed to ambient temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionthe crude residue was dissolved in EtOAc
  4. washwashed successively with saturated aqueous NaHCO3 and brine
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b39b7d4cc4a741b2b2da46d8c1d28fba
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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