HCID 131734380, compound → HCID 89616727, compound

HRID 1507698Notes

Reaction equation

HRID 1507698 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[S:35]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])(=[O:37])=[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]([S:35]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:43])([CH3:44])[CH3:42])(=[O:36])=[O:37])=[C:9]([OH:8])[C:13]=1[OH:14])=[O:26]

Participants

4

Reactant 1

HCID 131734380HCID 131734380, compound

Product 1

HCID 89616727HCID 89616727, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl (3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrol-2-yl)sulfonyl carbamate (10) (166 mg, 0.26 mmol) in methanol (2.5 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 tert-butyl (5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrol-2-yl)sulfonylcarbamate (UL1-030) (65 mg, 52%) as a yellow solid: m/z 456 (M+H)+ (ES+); 454 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 11.04 (s, 1H), 8.75 (s, 1H), 8.35 (s, 1H), 7.07-7.00 (m, 2H), 6.92-6.86 (m, 2H), 3.77 (s, 3H), 2.80 (br s, 6H), 1.35 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-3caf3b7c91f94c73b64a0ecc2c49111e
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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