Sodium Bicarbonate → 4-(Fmoc-amino)-1-methyl-1H-Imidazole-2-carboxylic Acid

HRID 1831031Notes

Reaction equation

HRID 1831031 reaction equation
Cl.C[O:3][C:4]([C:6]1[N:7]([CH3:12])[CH:8]=[C:9]([NH2:11])[N:10]=1)=[O:5].[C:13](=[O:16])([O-])[OH:14].[Na+].C(=O)([O-])ON1C(=O)CC([CH2:26][CH:27]2[C:39]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)C1=O>>[CH:29]1[C:28]2[CH:27]([CH2:26][O:14][C:13]([NH:11][C:9]3[N:10]=[C:6]([C:4]([OH:3])=[O:5])[N:7]([CH3:12])[CH:8]=3)=[O:16])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]=2[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 57362223Methyl 4-amino-1-methyl-1H-imidazole-2-carboxylate hydrochlorideHCID 71304114(9H-fluoren-9-yl)methyl-2,5-dioxopyrrolidin-1-yl carbonate

Product 1

HCID 70106984-(Fmoc-amino)-1-methyl-1H-Imidazole-2-carboxylic AcidYield 70.9%

Procedure

After dissolving 10 (8.24 g, 41.9 mmol) into distilled water (60 ml), sodium hydroxide (4.2 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 (200 ml, 1:1, v/v) to be used for the next reaction. After dissolving sodium hydrogen carbonate (14.1 g) into the solution, 9-fluorenylmethylsuccinimidyl carbonate (16.9 g, 50.1 mmol) was added thereto. After stirring the mixture overnight, precipitates were collected by filtration to obtain 12 (10.8 g, 29.7 mmol). After acidifying the filtrate with 10% hydrochloric acid, precipitates thus generated were collected by filtration and washed with ethyl acetate to further obtain 12 (1.2 g, 3.30 mmol). (Total yield: 12.0 g, 79%)

Workup

  1. distillationinto distilled water (60 ml), sodium hydroxide (4.2 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 (200 ml, 1:1
  5. customv/v) to be used for the next reaction
  6. additionwas added
  7. stirringAfter stirring the mixture overnight
  8. customprecipitates
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-e58512e1cbd04638b979e12e6420c237
Source dataset
uspto-grants-2006_06
Patent number
US07067622B2

Reaction notes

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