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

HRID 1965169Notes

Reaction equation

HRID 1965169 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:42])[CH:26]([NH:31][C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[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.CO>C(Cl)Cl>[CH2:35]([O:34][C:32](=[O:33])[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:42])[C:27]([CH3:30])([CH3:29])[CH3:28])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 676074394-(2-Benzyloxycarbonylamino-3,3-dimethyl-butyryl)-3-(3,4-difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

Product 1

HCID 67608719{1-[6-(3,4-Difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid benzyl esterYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The Boc-containing compound 23 (1.0 g, 1.70 mmol) was dissolved in DCM (4 mL) and cooled to 0° C. before TFA (2 mL) was added and the reaction stirred at 0° C. for 1 h. TLC analysis (10:1 DCM/MeOH) indicated the starting material had all been consumed and the product had formed. The reaction mixture was concentrated at low pressure on the rotary evaporator. The crude residue was dissolved in DCM and washed successively with saturated aqueous NaHCO3 (3×), and brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to afford 845 mg of 24 as a white foam. Mass spectrum, m/z [488.3] (M+H)+.

Workup

  1. additionwas added
  2. customall been consumed
  3. customthe product had formed
  4. concentrationThe reaction mixture was concentrated at low pressure on the rotary evaporator
  5. dissolutionThe crude residue was dissolved in DCM
  6. washwashed successively with saturated aqueous NaHCO3 (3×), and brine
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-300d8db8ee8743a88aac97e6f3e92512
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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