Trifluoroacetic acid → {2-[3-(Naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

HRID 446989Notes

Reaction equation

HRID 446989 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]2[N:13]([C:29](=[O:42])[CH2:30][NH:31][C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[CH2:14][CH:15]([C:16](=[O:28])[NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[CH:9]12)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:35]([O:34][C:32](=[O:33])[NH:31][CH2:30][C:29]([N:13]1[CH2:14][CH:15]([C:16](=[O:28])[NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[CH:9]2[NH:8][CH2:12][CH2:11][CH:10]12)=[O:42])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67281528HCID 67281528, compound

Product 1

HCID 67280980{2-[3-(Naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-carbamic acid benzyl esterYield 110.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 55 (400 mg, 0.69 mmol) in DCM (10 mL) was treated with TFA (3 mL) at ambient temperature. After 1 h, the solution was concentrated, diluted with EtOAc, and washed with saturated NaHCO3. The aqueous phase was back extracted with DCM and the combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 56 (360 mg) which was used without further purification. Mass spectrum, m/z [473.2] (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with saturated NaHCO3
  4. extractionThe aqueous phase was back extracted with DCM
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3f438e5a824d4bb1bf79a3e3f9f252d3
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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