Diisopropylethylamine → (S)-tert-butyl (1-((2-amino-5-iodophenyl)amino)-3,3-dimethyl-1-oxobutan-2-yl)carbamate
Reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[I:25][C:26]1[CH:27]=[C:28]([NH2:33])[C:29]([NH2:32])=[CH:30][CH:31]=1.[C:34]([O:38][C:39]([NH:41][C@@H:42]([C:46]([CH3:49])([CH3:48])[CH3:47])[C:43](O)=[O:44])=[O:40])([CH3:37])([CH3:36])[CH3:35].CCN(C(C)C)C(C)C>CN(C=O)C.O.CCOC(C)=O>[NH2:32][C:29]1[CH:30]=[CH:31][C:26]([I:25])=[CH:27][C:28]=1[NH:33][C:43](=[O:44])[C@@H:42]([NH:41][C:39](=[O:40])[O:38][C:34]([CH3:37])([CH3:36])[CH3:35])[C:46]([CH3:49])([CH3:48])[CH3:47]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
HATU (16.25 g, 42.7 mmol) was added to a stirred solution of 4-iodobenzene-1,2-diamine (10 g, 42.7 mmol), (S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoic acid (9.88 g, 42.7 mmol) and DIPEA (14.93 mL, 85 mmol) in DMF (120 mL) at 0° C. and the reaction mixture was stirred at rt for 12 h. The reaction mixture was diluted with water and EtOAc. The organic layer was washed with water, 10% NaHCO3 solution, brine, dried over Na2SO4 and concentrated to yield (S)-tert-butyl (1-((2-amino-5-iodophenyl)amino)-3,3-dimethyl-1-oxobutan-2-yl)carbamate (20 g). LC/MS (Condition B-10): Rt=1.94 min. LC/MS: Anal. Calcd. for [M+H]+ C17H27IN3O3: 448.10; found 448.2.
Workup
- washThe organic layer was washed with water, 10% NaHCO3 solution, brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a9e4620bc68d4a2bbc9127b78762ffa9
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09326973B2
Reaction notes
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