Potassium tert-butoxide → HCID 68428371, compound
Reaction equation
C([O:3][C:4]([C:6]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[C:9]([Br:15])[N:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:7]=1[CH2:23][N:24]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=O)C.CC([O-])(C)C.[K+]>C1COCC1>[CH2:29]([O:28][C:26]([CH:25]1[N:24]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:23][C:7]2[N:8]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:9]([Br:15])=[C:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[C:6]=2[C:4]1=[O:3])=[O:27])[CH3:30]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 5-bromo-2-[(tert-butoxycarbonyl-ethoxycarbonylmethyl-amino)-methyl]-4-tert-butyl-1-(4-fluoro-phenyl)-1H-pyrrole-3-carboxylic acid ethyl ester (4.0 g, ˜6.28 mmol) in THF (15 mL) at −78° C. was added a solution of KOtBu in THF (9.42 mL, 9.42 mmol, 1 M); the reaction was stirred for 30 min at −78° C. and for 30 at room temperature. The reaction was subsequently quenched with saturated ammonium chloride aqueous solution, extracted with EtOAc, washed with water, and saturated NaCl aqueous solution, dried over anhydrous sodium sulfate, filtered, concentrated, to give an oil, the title product (3.24 g, crude), which was not further purified. The title product, 1H NMR (200 MHz, CDCl3): δ (ppm)=4.4-7.0 (m, 4H), 4.5-4.1 (m, 5H), 1.6-1.2 (m, 21H).
Workup
- customThe reaction was subsequently quenched with saturated ammonium chloride aqueous solution
- extractionextracted with EtOAc
- washwashed with water, and saturated NaCl aqueous solution
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give an oil
Sources & evidence
- ORD record
- ord-5263959b11e1488fa93f5b2ba2286f0e
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696223B2
Reaction notes
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