Sodium Carbonate → 4-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)-1-methyl-1H-pyrrole-2-carboxylic acid

HRID 1831030Notes

Reaction equation

HRID 1831030 reaction equation
Cl.C[O:3][C:4]([C:6]1[N:7]([CH3:12])[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[CH:19]1[C:31]2[CH:30]([CH2:32][O:33][C:34](Cl)=[O:35])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH:22]=[CH:21][CH:20]=1>>[CH:19]1[C:31]2[CH:30]([CH2:32][O:33][C:34]([NH:11][C:9]3[CH:10]=[C:6]([C:4]([OH:3])=[O:5])[N:7]([CH3:12])[CH:8]=3)=[O:35])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 2794656methyl 4-amino-1-methyl-1H-pyrrole-2-carboxylate hydrochloride

Product 1

HCID 27561594-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)-1-methyl-1H-pyrrole-2-carboxylic acidYield 59.6%

Procedure

After dissolving 9 (10.9 g, 57.2 mmol) into distilled water (80 ml), sodium hydroxide (9.2 g) was added to the solution. After stirring overnight, the solution was neutralized with 1N hydrochloric acid, followed by distillation under a reduced pressure. The residue was dissolved into a mixed solution of water and ethyleneglycoldimethylether (100 ml, 1:1, v/v) to be used for next reaction. After dissolving sodium carbonate (5.3 g) into the solution, 9-fluorenylmethylchloroformate (17.8 g, 68.6 mmol) was added thereto. After stirring the mixture overnight, precipitates were collected by filtration to obtain 11 (12.3 g, 34.1 mmol). The filtrate was added to a mixed solution of 1M sodium carbonate solution and diethylether (1:1, v/v). Precipitates were collected by filtration to further obtain 11 (3.4 g). After acidifying the water layer with 10% hydrochloric acid, the water layer was extracted with ethyl acetate. The organic layer was distilled under a reduced pressure and then recrystallized with hexane-dioxane to further obtain 11 (1.6 g). (Total yield: 17.3 g, 84%)

Workup

  1. distillationinto distilled water (80 ml), sodium hydroxide (9.2 g)
  2. additionwas added to the solution
  3. distillationfollowed by distillation under a reduced pressure
  4. dissolutionThe residue was dissolved into a mixed solution of water and ethyleneglycoldimethylether (100 ml, 1:1
  5. customv/v) to be used for next reaction
  6. additionwas added
  7. stirringAfter stirring the mixture overnight
  8. customprecipitates
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-02de7e771b364de28739d1fe22c9c2b6
Source dataset
uspto-grants-2006_06
Patent number
US07067622B2

Reaction notes

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