HCID 89610400, compound → HCID 71599539, compound

HRID 1507695Notes

Reaction equation

HRID 1507695 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]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:10]=1[C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])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]([O:33][CH3:34])=[CH:31][CH:32]=2)[C:10]([C:35]([O:37][CH:38]([CH3:39])[CH3:40])=[O:36])=[C:9]([OH:8])[C:13]=1[OH:14])=[O:26]

Participants

4

Reactant 1

HCID 89610400HCID 89610400, compound

Product 1

HCID 71599539HCID 71599539, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of isopropyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (8) (130 mg, 0.240 mmol) in methanol (5 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 30° C. under H2 (full H2 mode). The output was concentrated in vacuo to afford isopropyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (UL1-035) (69 mg, 79%) as a white solid: m/z 363 (M+H)+ (ES+); 361 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 8.60 (s, 1H), 8.42 (s, 1H), 7.10-6.99 (m, 2H), 6.91-6.82 (m, 2H), 4.83 (sept., J=6.2 Hz, 1H), 3.77 (s, 3H), 2.83 (br s, 6H), 0.96 (d, J=6.2 Hz, 6H).

Workup

  1. customat 30° C.
  2. concentrationThe output was concentrated in vacuo

Sources & evidence

ORD record
ord-62d2ccc8255a4593b2181459d72bc050
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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