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

HRID 1965165Notes

Reaction equation

HRID 1965165 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]2[N:20]([C:23](=[O:45])[CH:24]([NH:28][C:29](=[O:44])[CH:30]([N:32]([C:34]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])[CH3:33])[CH3:31])[CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:22][CH:9]12)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:37]([O:36][C:34](=[O:35])[N:32]([CH3:33])[CH:30]([C:29](=[O:44])[NH:28][CH:24]([C:23]([N:20]1[CH2:21][CH2:22][CH:9]2[NH:8][CH2:12][CH:11]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]12)=[O:45])[CH:25]([CH3:27])[CH3:26])[CH3:31])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 676088904-{2-[2-(Benzyloxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyryl}-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

Product 1

HCID 67608270Methyl-{1-[2-methyl-1-(6-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl)-propylcarbamoyl]-ethyl}-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution containing 16 (370 mg, 0.59 mmol) in DCM (10 mL) was added TFA (4 mL) at 0° C. After 1 h, the reaction mixture was diluted with DCM and the resultant organic solution was washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford crude 18 which was used without further purification.

Workup

  1. washthe resultant organic solution was washed successively with saturated aqueous NaHCO3 and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford crude 18 which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-0045ef04a9464d998ba1774661abd126
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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