Sodium Hydroxide → 4-(4-((tert-Butoxycarbonyl)amino)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid

HRID 476391Notes

Reaction equation

HRID 476391 reaction equation
C(C1NC=CC=1)(OC(C)(C)C)=O.[C:13]([O:17][C:18]([NH:20][C:21]1[CH:22]=[C:23]([C:27]([NH:29][C:30]2[CH:31]=[C:32]([C:36]([O:38]C)=[O:37])[N:33]([CH3:35])[CH:34]=2)=[O:28])[N:24]([CH3:26])[CH:25]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[OH-].[Na+]>CO>[C:13]([O:17][C:18]([NH:20][C:21]1[CH:22]=[C:23]([C:27]([NH:29][C:30]2[CH:31]=[C:32]([C:36]([OH:38])=[O:37])[N:33]([CH3:35])[CH:34]=2)=[O:28])[N:24]([CH3:26])[CH:25]=1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10523563methyl 4-(4-(tert-butoxycarbonylamino)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylateHCID 1545894776369-00-1

Product 1

HCID 107611254-(4-((tert-Butoxycarbonyl)amino)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acidYield 102.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of Boc pyrrole dimer (3) (0.805 g, 2.1 mmol) in MeOH (40 mL) was treated with 1M NaOH solution (25 mL). The reaction mixture was stirred at room temperature for 18 hours. The volume was reduced in vacuo and the aqueous solution extracted with EtOAc (50 mL). The solvent was removed from the EtOAc fraction and the residue was treated with 1M NaOH solution (10 mL) for a further 3 hours. This was combined with the previous aqueous fraction and acidified to pH2-3 with 1M HCl solution and the suspension extracted with EtOAc (3×75 mL). The organic fractions were combined, dried over MgSO4 and concentrated in vacuo to give a yellow foam 0.781 g (100%). 1H NMR d6-DMSO δ 12.07 (1H, bs, OH), 9.81 (1H, s, N—H), 9.08 (1H, s, N—H), 7.40 (1H, d, J=1.9 Hz, Py-H), 6.88 (1H, s, Py-H), 6.84 (1H, s, Py-H), 6.83 (1H, s, Py-H), 3.81 (3H, s, N—CH3), 3.80 (3H, s, N—CH3), 1.45 (9H, s, Boc-H); 13C NMR d6-DMSO δ 171.9, 161.9, 158.3, 152.8, 122.6, 122.3, 120.2 (CH), 119.4, 117.0 (CH), 108.3 (CH), 103.7 (CH), 78.3, 36.1 (CH3), 36.1 (CH3), 28.1 ([CH3]3).

Workup

  1. extractionthe aqueous solution extracted with EtOAc (50 mL)
  2. customThe solvent was removed from the EtOAc fraction
  3. additionthe residue was treated with 1M NaOH solution (10 mL) for a further 3 hours
  4. extractionthe suspension extracted with EtOAc (3×75 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b6d683dc38b48078419ac4b5025dc9f
Source dataset
uspto-grants-2014_01
Patent number
US08637664B2

Reaction notes

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