Trifluoroacetic acid → 4-(2-Amino-2-cyclohexyl-acetyl)-3-phenylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

HRID 446977Notes

Reaction equation

HRID 446977 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([C:16](=[O:24])[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]2[N:25]([C:28](=[O:44])[CH:29]([NH:36]C(OC(C)(C)C)=O)[CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:26][CH2:27][CH:12]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([C:16](=[O:24])[NH:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:13]2[N:25]([C:28](=[O:44])[CH:29]([NH2:36])[CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:26][CH2:27][CH:12]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 672814864-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-3-phenylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Product 1

HCID 672809194-(2-Amino-2-cyclohexyl-acetyl)-3-phenylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl esterYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 39 (460 mg, 0.76 mmol) in DCM (10 mL) was cooled to 0° C. and treated with TFA (4 mL). After 2 h, the solution was concentrated, diluted with EtOAc and washed with saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 40 (366 mg) as a pale yellow-colored foam that was used without further purification. Mass spectrum, m/z [505.5] (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with saturated aqueous NaHCO3, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-13f7ceb41fa74ebd820ea7fa82aa3abe
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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