HCID 89610373, compound → HCID 89610495, compound

HRID 1507718Notes

Reaction equation

HRID 1507718 reaction equation
[NH2:1][C:2](=[O:36])[CH2:3][O:4][C:5]1[C:9]([O:10]CC2C=CC=CC=2)=[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:7]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:6]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32]>CO.[Pd]>[NH2:1][C:2](=[O:36])[CH2:3][O:4][C:5]1[C:9]([OH:10])=[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:7]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:6]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

4

Reactant 1

HCID 89610373HCID 89610373, compound

Product 1

HCID 89610495HCID 89610495, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Diethyl 3-(2-amino-2-oxoethoxy)-4-(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate (25) (66 mg, 0.133 mmol) in MeOH (66 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 20° C. under H2 (full H2 mode). The output was concentrated in vacuo to afford a yellow oil. The residue was purified by silica gel chromatography (4 g, 0-100% EtOAc in isohexane) to afford diethyl 3-(2-amino-2-oxoethoxy)-4-hydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate (UL2-031) (25 mg, 46%) as a white solid: m/z 407 (M+H)+ (ES+); 405 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 9.61 (s, 1H), 7.82-7.63 (m, 2H), 7.10-7.06 (m, 2H), 6.93-6.84 (m, 2H), 4.49 (s, 2H), 4.03-3.93 (m, 4H), 3.79 (s, 3H), 1.05-0.94 (m, 6H).

Workup

  1. customat 20° C.
  2. concentrationThe output was concentrated in vacuo
  3. customto afford a yellow oil
  4. customThe residue was purified by silica gel chromatography (4 g, 0-100% EtOAc in isohexane)

Sources & evidence

ORD record
ord-18bb33bb312a4af696eb173c74c24f78
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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