Trifluoroacetic acid → 4-(2-Amino-2-cyclohexyl-acetyl)-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid (1-phenyl-ethyl)-amide

HRID 446971Notes

Reaction equation

HRID 446971 reaction equation
C(OC(=O)[NH:7][CH:8]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[C:9]([N:11]1[CH2:15][CH2:14][CH:13]2[N:16]([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:17][CH:18]([C:19](=[O:29])[NH:20][CH:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:22])[CH:12]12)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:23]1([CH:21]([NH:20][C:19]([CH:18]2[CH2:17][N:16]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:13]3[CH2:14][CH2:15][N:11]([C:9](=[O:10])[CH:8]([NH2:7])[CH:34]4[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]4)[CH:12]23)=[O:29])[CH3:22])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67282347{1-Cyclohexyl-2-[4-methanesulfonyl-6-(1-phenyl-ethylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 672815224-(2-Amino-2-cyclohexyl-acetyl)-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid (1-phenyl-ethyl)-amideYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 30 (81 mg, 0.14 mmol) in DCM (10 mL) was treated with TFA (3 mL) at 0° C. After 1 h, the reaction mixture was warmed to ambient temperature. After 30 min, the solution was concentrated, diluted with EtOAc, washed with saturated NaHCO3, and brine. The aqueous layers were back-extracted with DCM and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated to afford 31 (60 mg) as an off-white foam. 1H NMR (CDCl3, 300 MHz): δ7.42-7.27 (m, 5H), 5.10-5.01 (m, 1H), 4.57 (d, J=4.5 Hz, 1H), 4.22 (m, 1H), 3.86 (d, J=11.1 Hz, 1H), 3.78 (m, 1H), 3.64-3.46 (m, 2H), 3.19 (m, 1H), 2.96 (s, 3H), 2.62-2.56 (m, 1H), 1.77-1.67 (m, 6H), 1.53 (d, J=6.9 Hz, 3H), 1.19-1.15 (m, 6H) ppm. Mass spectrum, m/z [477.5] (M+H)+.

Workup

  1. waitAfter 30 min
  2. concentrationthe solution was concentrated
  3. additiondiluted with EtOAc
  4. washwashed with saturated NaHCO3, and brine
  5. extractionThe aqueous layers were back-extracted with DCM
  6. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3f468515acd6482abd1abfe0889e51f0
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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