HCID 59292944, compound → 2-Amino-4-diethoxymethyl-imidazole-1-carboxylic acid tert-butyl ester

HRID 2391932Notes

Reaction equation

HRID 2391932 reaction equation
Br[CH2:2][C:3](=O)[CH:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].[C:12]([O:16][C:17]([NH:19][C:20]([NH2:22])=[NH:21])=[O:18])([CH3:15])([CH3:14])[CH3:13]>>[C:12]([O:16][C:17]([N:19]1[CH:2]=[C:3]([CH:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])[N:21]=[C:20]1[NH2:22])=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

3

Reactant 2

HCID 59292944HCID 59292944, compoundHCID 178454308HCID 178454308, compound

Product 1

HCID 592928212-Amino-4-diethoxymethyl-imidazole-1-carboxylic acid tert-butyl esterYield 41.7%

Conditions

Temperature
50 °C

Procedure

A mixture of 3-bromo-1,1-diethoxy-propan-2-one (21.3 g, 95 mmol) (Step 179.9) and N-tert-butoxycarbonylguanidine (45.3 g, 284 mmol, 3 equiv) (Step 179.10) was stirred at 50° C. for 8 h. The reaction mixture was concentrated, diluted in EtOAc/H2O and extracted with EtOAc. The organic phase was washed with water and brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography (DCM/EtOAc, 3:7) followed by trituration in Et2O to afford 11.3 g of the title compound as a white solid: ES-MS: 286 [M+H]+; Rf=0.34 (DCM/EtOAc, 3:7).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted in EtOAc/H2O
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (DCM/EtOAc, 3:7)

Sources & evidence

ORD record
ord-f2f89d7c0e994af8b953919078055444
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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