Ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylate → ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylate
Reaction equation
C([O:8][C:9]1[C:13]([O:14]CC2C=CC=CC=2)=[C:12]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)[C:10]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35])C1C=CC=CC=1>CO.[Pd]>[CH3:25][N:23]([CH3:24])[C:22]([C:12]1[N:11]([C:27]2[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=2)[C:10]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:9]([OH:8])[C:13]=1[OH:14])=[O:26]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylate (36) (30 mg, 0.06 mmol) in MeOH (2 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 25° C. under H2 (full H2 mode). The output was concentrated in vacuo, and a solid was collected by filtration after trituration with isohexane to afford ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylate (UL1-100) (11 mg, 56%) as a yellow solid: m/z 335 (M+H)+ (ES+), 333 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 9.50 (s, 1H), 8.54 (s, 1H), 8.42 (s, 1H), 6.94-6.86 (m, 2H), 6.69-6.62 (m, 2H), 3.99 (q, J=7.0 Hz, 2H), 2.81 (br s, 6H), 0.98 (t J=7.0 Hz, 3H).
Workup
- customat 25° C.
- concentrationThe output was concentrated in vacuo
- filtrationa solid was collected by filtration after trituration with isohexane
Sources & evidence
- ORD record
- ord-8f09b154d0bc4dfa8cba14085bdf9091
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221756B2
Reaction notes
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