Trifluoroacetic acid → 4-(2-Amino-2-cyclohexyl-acetyl)-1-cyclopropanecarbonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide

HRID 446983Notes

Reaction equation

HRID 446983 reaction equation
C(OC(=O)[NH:7][CH:8]([CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)[C:9]([N:11]1[CH2:15][CH2:14][CH:13]2[N:16]([C:32]([CH:34]3[CH2:36][CH2:35]3)=[O:33])[CH2:17][CH:18]([C:19](=[O:31])[NH:20][CH:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:24][CH2:23][CH2:22]3)[CH:12]12)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:21]1([NH:20][C:19]([CH:18]2[CH2:17][N:16]([C:32]([CH:34]3[CH2:35][CH2:36]3)=[O:33])[CH:13]3[CH2:14][CH2:15][N:11]([C:9](=[O:10])[CH:8]([NH2:7])[CH:37]4[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]4)[CH:12]23)=[O:31])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67280896{1-Cyclohexyl-2-[4-cyclopropanecarbonyl-6-(1,2,3,4-tetrahydro-naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 672813634-(2-Amino-2-cyclohexyl-acetyl)-1-cyclopropanecarbonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amideYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 46 (430 mg, 0.72 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 DCM and washed successively with saturated aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 47 (332 mg) as a white foam that was used without further purification. Mass spectrum, m/z [493.7] (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-2f2e3911efa24d00a2dd7f03b8bf8fe4
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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