Hydrochloric Acid → HCID 89610614, compound

HRID 1507684Notes

Reaction equation

HRID 1507684 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22]([O:24]CC)=[O:23])[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]CC)=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C1COCC1.Cl>C(O)C>[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22]([OH:24])=[O:23])[N:11]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[C:10]=1[C:35]([OH:37])=[O:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 89610390HCID 89610390, compound

Product 1

HCID 89610614HCID 89610614, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate (1) (2.8 g, 5.29 mmol), 2M NaOH (aq.) (26.4 mL, 52.9 mmol), in ethanol (12 mL) and THF (20 mL) was stirred at 60° C. for 72 h. After cooling to RT, the mixture was acidified with 6M HCl (aq.) and the resulting precipitate was collected by filtration, washed with water (5 mL), and Et2O (5 mL) to afford 4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid (2) (1.94 g, 67%) as an off-white solid: m/z 474 (M+H)+ (ES+); 472 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ 12.61 (s, 2H), 7.46-7.40 (m, 4H), 7.39-7.29 (m, 6H), 7.16-7.07 (m, 2H), 6.92-6.84 (m, 2H), 5.07 (s, 4H), 3.78 (s, 3H).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water (5 mL), and Et2O (5 mL)

Sources & evidence

ORD record
ord-a25d3b27e77444d3bd48088ab496410c
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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