Sodium Hydroxide → 4-[(tert-Butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid

HRID 1968480Notes

Reaction equation

HRID 1968480 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]([O:17]C)=[O:16])[N:12]([CH3:14])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.O.O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]([OH:17])=[O:16])[N:12]([CH3:14])[CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11345817Methyl 4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 27356364-[(tert-Butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acidYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 4-(tert-butoxycarbonylamino)-1-methyl-1H-pyrrole-2-carboxylate (Eldon E. Baird and Peter B. Dervan, J. Am. Chem. Soc. 1996, 118, 6141-6146) (5.0 g, 19.67 mmol) in 120 ml of 1:1 THF/H2O was added 8 g of NaOH in 30 ml of water. The mixture was stirred overnight, concentrated, diluted with water, extracted with EtAc/Hexane (1:1). The aqueous solution was adjusted to pH 4.0 with 20% H3PO4 and extracted with EtAc (4×60 ml). The organic solutions were combined, dried over MgSO4, filtered, evaporated and crystallized with ethanol/EtAc/Hexane to afford 3.81 g (81%) of the title product. 1H NMR (CD3OD) 12.79 (s, 1H), 10.48 (br, 1H), 7.51 (s, 1H), 6.99 (s, 1H), 3.78 (s, 3H), 1.49 (s, 9H); 13C NMR 158.47, 153.82, 123.64, 121.56, 109.58, 79.52, 37.06, 28.42; MS m/z− 239.2 (M−H).

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted with EtAc/Hexane (1:1)
  4. extractionextracted with EtAc (4×60 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customcrystallized with ethanol/EtAc/Hexane

Sources & evidence

ORD record
ord-490afae18ba74268b106cf5f2e7c75f5
Source dataset
uspto-grants-2013_04
Patent number
US08426402B2

Reaction notes

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