Lithium Hydroxide → 3-Chloro-5-[(cyclopropylamino)carbonyl]-1H-pyrrole-2-carboxylic acid

HRID 1874971Notes

Reaction equation

HRID 1874971 reaction equation
[Li+].[OH-].[Cl:3][C:4]1[CH:8]=[C:7]([C:9]([NH:11][CH:12]2[CH2:14][CH2:13]2)=[O:10])[NH:6][C:5]=1[C:15]([O:17]C)=[O:16]>C1COCC1.CO>[Cl:3][C:4]1[CH:8]=[C:7]([C:9]([NH:11][CH:12]2[CH2:13][CH2:14]2)=[O:10])[NH:6][C:5]=1[C:15]([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68484245Methyl 3-chloro-5-[(cyclopropylamino)carbonyl]-1H-pyrrole-2-carboxylate

Product 1

HCID 684836053-Chloro-5-[(cyclopropylamino)carbonyl]-1H-pyrrole-2-carboxylic acidYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (1 N in water, 2 mL, 2 mmol) was added to a solution of methyl 3-chloro-5-[(cyclopropylamino)carbonyl]-1H-pyrrole-2-carboxylate (0.0992 g, 0.409 mmol) in THF (2 mL) and methanol (2 mL) and the solution was stirred at RT overnight. The reaction mixture was evaporated to a residue and partitioned between EtOAc and 1 N HCl. The organic layer was separated, dried over MgSO4 and evaporated to a solid to afford the title compound (0.072 g, 77%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.08 (s, 1H), 12.05 (br. s., 1H), 8.32 (d, 1H), 6.73 (d, 1H), 2.71-2.81 (m, 1H), 0.62-0.72 (m, 2H), 0.42-0.53 (m, 2H). LCMS: m/z 229.2 (M+1).

Workup

  1. customThe reaction mixture was evaporated to a residue
  2. custompartitioned between EtOAc and 1 N HCl
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customevaporated to a solid

Sources & evidence

ORD record
ord-7e9dcf15d5c046df914944f4c47ad582
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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