HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (S)-tert-butyl (1-((2-amino-5-iodophenyl)amino)-3,3-dimethyl-1-oxobutan-2-yl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid | HCID 2734668 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 4-Iodobenzene-1,2-diamine | HCID 11207049 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (S)-tert-butyl (1-((2-amino-5-iodophenyl)amino)-3,3-dimethyl-1-oxobutan-2-yl)carbamate | HCID 86690085 | 104.7% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09326973B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-a9e4620bc68d4a2bbc9127b78762ffa9 |
| Source note | uspto-grants-2016_05 |