Water → methyl 1-((ethoxycarbonyl)amino)-3-phenyl-1H-pyrrole-2-carboxylate

HRID 2170141Notes

Reaction equation

HRID 2170141 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:3]1[C:13]([O:15][CH3:16])=[O:14].[CH2:17]([O:19][C:20](Cl)=[O:21])[CH3:18].O>C(Cl)Cl>[CH2:17]([O:19][C:20]([NH:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:3]1[C:13]([O:15][CH3:16])=[O:14])=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 10928Ethyl chloroformateHCID 90386150HCID 90386150, compound

Product 1

HCID 90386155methyl 1-((ethoxycarbonyl)amino)-3-phenyl-1H-pyrrole-2-carboxylateYield 37.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 1-amino-3-phenyl-1H-pyrrole-2-carboxylate (0.200 g, 0.925 mmol) was dissolved in CH2Cl2 (20 mL) and then was added TEA (0.387 mL, 2.77 mmol), followed by ethylchloroformate (0.0890 mL, 0.925 mmol). The reaction mixture was stirred at room temperature for overnight. Water (50 mL) was added to reaction mixture and the aqueous mixture was extracted with CH2Cl2 (25×2 mL). The organic layer separated and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using CombiFlash (REDISEP®, silica gel, 24 g, 15% EtOAc/hexanes) to afford methyl 1-((ethoxycarbonyl)amino)-3-phenyl-1H-pyrrole-2-carboxylate (0.100 g, 37.5%). LCMS Condition B-39: retention time 2.14 min, [M+1]=289.0.

Workup

  1. extractionthe aqueous mixture was extracted with CH2Cl2 (25×2 mL)
  2. customThe organic layer separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-09c3567af70f415faeef2a106cf15175
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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