(3aR,6aR)-1-(4'-Cyano-biphenyl-4-yl)-hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic acid benzyl ester → HCID 44221502, compound
Reaction equation
C(OC([N:11]1[CH2:18][C@@H:17]2[C@@H:13]([N:14]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=4)=[CH:21][CH:20]=3)[CH2:15][CH2:16]2)[CH2:12]1)=O)C1C=CC=CC=1>FC(F)(F)C(O)=O>[N:14]1([C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[CH2:15][CH2:16][C@@H:17]2[CH2:18][NH:11][CH2:12][C@H:13]12Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The product of Example 1D ((3aR,6aR)-1-(4′-Cyano-biphenyl-4-yl)-hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic acid benzyl ester) (750 mg, 1.77 mmole) was refluxed in 10 ml trifluoroacetic acid for 2.5 hours. The solution was concentrated and triturated with dichloromethane. The residue was redissolved in dichloromethane and stirred with sodium bicarbonate powder. The solution was loaded on a silica gel column and purified by chromatography (0.6% ammonium hydroxide and 6% methanol in dichloromethane) to provide the title compound (330 mg, 64%). 1H NMR (CDCl3) δ ppm 7.64 (d, J=2.71 Hz, 4H) 7.51 (d, J=8.81 Hz, 2H) 6.66 (d, J=8.82 Hz, 2H) 4.07-4.17 (m, 1H) 3.50-3.65 (m, 1H) 3.24-3.36 (m, 1H) 2.86-3.10 (m, 5H) 2.15-2.29 (m, 1H) 1.74-1.93 (m, 1H). MS: (M+H)+=290.
Workup
- concentrationThe solution was concentrated
- customtriturated with dichloromethane
- dissolutionThe residue was redissolved in dichloromethane
- custompurified by chromatography (0.6% ammonium hydroxide and 6% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-9a1af63f8c8a4f99873f8735938ff578
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399468B2
Reaction notes
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