Trifluoroacetic acid → 2-Amino-1-[4-(2-amino-2-cyclohexyl-acetyl)-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-cyclohexyl-ethanone

HRID 1949661Notes

Reaction equation

HRID 1949661 reaction equation
C(OC(=O)[NH:7][CH:8]([CH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1)[C:9]([N:11]1[CH2:15][CH2:14][CH:13]2[N:16]([C:29](=[O:45])[CH:30]([NH:37]C(OC(C)(C)C)=O)[CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:17][CH:18]([C:19]3[C:27]4[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH:12]12)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]([CH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1)[C:9]([N:11]1[CH2:15][CH2:14][CH:13]2[N:16]([C:29](=[O:45])[CH:30]([NH2:37])[CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:17][CH:18]([C:19]3[C:27]4[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH:12]12)=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67407842{2-[4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 674121332-Amino-1-[4-(2-amino-2-cyclohexyl-acetyl)-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-cyclohexyl-ethanoneYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 121 (370 mg, 0.51 mmol) in DCM (10 mL) at 0° C. was added TFA (4 mL). After 2 h, the reaction mixture was concentrated in vacuo. The residue was dissolved in DCM and the organic solution was washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 210 mg of 122 which was used without further purification. Mass spectrum, m/z [523.3] (M)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in DCM
  3. washthe organic solution was washed successively with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1dfa6b6634fe417db0aba7886e7f1303
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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