Butyl isocyanate → N-(Butylamino)carbonyl-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide
Reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:17]=[C:16]([CH2:18][CH:19]([CH3:21])[CH3:20])[S:15][C:14]=3[S:22]([NH2:25])(=[O:24])=[O:23])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+].[CH2:28]([N:32]=[C:33]=[O:34])[CH2:29][CH2:30][CH3:31].C(NS(C1SC(CC(C)C)=CC=1C1C=CC(CN2C=CN=C2)=CC=1)(=O)=O)(C)(C)C>CC(C)=O.C(OCC)(=O)C>[CH2:28]([NH:32][C:33]([NH:25][S:22]([C:14]1[S:15][C:16]([CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:17][C:13]=1[C:10]1[CH:11]=[CH:12][C:7]([CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:8][CH:9]=1)(=[O:24])=[O:23])=[O:34])[CH2:29][CH2:30][CH3:31]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The crude product from step (c) above was dissolved in acetone (5 mL) under N2 (g). NaOH (0.20 mL, 1M, 0.20 mmol) was added to the mixture, which was then stirred for 10 min. Butyl isocyanate (109 μL, 0.97 mmol) was then added and the mixture was stirred overnight at room temperature. The reaction mixture was then diluted with ethyl acetate (150 mL) and washed with water and brine. The organic phase was dried over MgSO4 and the solvent was removed in vacuo. Purification using column chromatography with CHCl3:MeOH (10:1) as eluent yielded the title compound (15.1 mg, 0.032 mmol) in 33% yield (from 3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonic acid tert-butylamide).
Workup
- stirringthe mixture was stirred overnight at room temperature
- washwashed with water and brine
- dry with materialThe organic phase was dried over MgSO4
- customthe solvent was removed in vacuo
- customPurification
Sources & evidence
- ORD record
- ord-f349ccd448764fecb3e7ee660c57d58a
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124638B2
Reaction notes
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