Acetic Acid → HCID 67068492, compound
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([Br:12])[C:10]=1[NH2:11])=[O:5])[CH3:2].[CH:13](=O)[CH:14]([CH3:16])[CH3:15].[BH3-]C#N.[Na+].CC(O)=O.[OH-].[Na+]>C(Cl)Cl.CO>[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([Br:12])[C:10]=1[NH:11][CH2:13][CH:14]([CH3:16])[CH3:15])=[O:5])[CH3:2]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Amino-4-bromo-1H-pyrrole-2-carboxylic acid ethyl ester (0.136 g, 0.58 mmol) and isobutyraldehyde (0.067 g, 0.93 mmol) were stirred in CH2Cl2/MeOH (1:1, 3 mL) at r.t. for 2 h. NaCNBH3 (0.065 g, 1.04 mmol) and HOAc (0.035 g, 0.58 mmol) were added and the mixture was stirred at r.t. for 2 h and then stirred at 50° C. for 16 h. Additional isobutyraldehyde (1 equiv.) and NaCNBH3 (0.5 equiv.) were added and the mixture was continued stirring at 50° C. overnight. The reaction mixture was neutralized with 2 M NaOH solution and the solvents were removed in vacuo. The residue was taken up in ethyl acetate and extracted with water. The organic layer was dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (heptane/ethyl acetate gradient, 0 to 30% ethyl acetate), obtaining the title compound (0.040 g, 24%) as a white solid.
Workup
- stirringstirred at 50° C. for 16 h
- stirringthe mixture was continued stirring at 50° C. overnight
- customthe solvents were removed in vacuo
- extractionextracted with water
- dry with materialThe organic layer was dried (Na2SO4)
- concentrationconcentrated
- customThe crude product was purified by flash chromatography (heptane/ethyl acetate gradient, 0 to 30% ethyl acetate)
Sources & evidence
- ORD record
- ord-2d9b3c421cbe44938460dbd1e202c417
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859568B2
Reaction notes
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