Water → 2,3-Diethyl 1-amino-5-(1-methylethyl)-1H-pyrrole-2,3-dicarboxylate

HRID 2108353Notes

Reaction equation

HRID 2108353 reaction equation
[CH:1]([C:4]1[NH:8][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=1)([CH3:3])[CH3:2].[H-].[Na+].[NH2:21]Cl.O>CN(C=O)C.CCOCC>[NH2:21][N:8]1[C:4]([CH:1]([CH3:2])[CH3:3])=[CH:5][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 25423MonochloramineHCID 57629467HCID 57629467, compound

Product 1

HCID 576294792,3-Diethyl 1-amino-5-(1-methylethyl)-1H-pyrrole-2,3-dicarboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1B (2.53 g, 10 mmol) in dry DMF (40 ml) was added NaH (60%, 550 mg, 13.75 mmol) in one portion. After H2 evolution subsided, NH2Cl in ether (85 ml) was added dropwise via additional funnel. The reaction mixture was stirred at room temperature for 1 h. Water was added, the mixture was extracted with ether (×3), the combined ether layers were washed with brine, dried over MgSO4, concentrated in vacuo to give 1C (2.50 g, 93%) as an oil. Compound 1C had an analytical HPLC retention time=2.893 min. (Chromolith SpeedROD column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 ml/min, monitoring at 220 nm) and a LC/MS M++1=269+.

Workup

  1. extractionthe mixture was extracted with ether (×3)
  2. washthe combined ether layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d10ec594b5a477ab12ba10c04919890
Source dataset
uspto-grants-2009_04
Patent number
US07514435B2

Reaction notes

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