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

HRID 476391노트

반응식

HRID 476391 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3b6d683dc38b48078419ac4b5025dc9f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637664B2

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