3-Bromo-1,1-diethoxypropan-2-one → 2-Amino-4-diethoxymethyl-imidazole-1-carboxylic acid tert-butyl ester

HRID 2409783Notes

Reaction equation

HRID 2409783 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 592929443-Bromo-1,1-diethoxypropan-2-oneHCID 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-40904f6ae67b4a1f88e8585f3b09717c
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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