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

HRID 2403487Notes

Reaction equation

HRID 2403487 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N: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[N: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 11379828METHYL 4-(TERT-BUTOXYCARBONYLAMINO)-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE

Product 1

HCID 27572264-[(tert-Butoxycarbonyl)amino]-1-methyl-1H-imidazole-2-carboxylic acidYield 81.5%

Reagents, catalysts & solvents 2

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

Procedure

Methyl 4-(tert-butoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxylate (5.0 g, 19.59 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 3.85 g (81%) of the title product. 1H NMR (DMSO) 9.32 (s, 1H), 7.29 (s, 1H), 3.57 (s, 3H), 1.42 (s, 9H); 13C NMR 172.45, 159.78, 136.93, 135.44, 132.85, 79.50, 35.57, 28.07; MS m/z−240.8 (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-f69e69f107f94a148f95e51bf9a4557e
Source dataset
uspto-grants-2014_08
Patent number
US08802667B2

Reaction notes

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