Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid | HCID 7009590 | — |
| 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 | 1-[(2S)-2-Amino-3-methyl-1-oxobutyl]-N-ethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide | HCID 117873111 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 131735257 | HCID 131735257 | 78.5% |
Reaction Steps
To a solution of (S)-2-(tert-butoxycarbonyl(methyl)amino)propanoic acid (40.9 mg, 201 μmol, Eq: 1.5) and 1-((S)-2-amino-3-methylbutanoyl)-N-ethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (39 mg, 134 μmol, Eq: 1.00) in DMF (1 mL) was added HATU (76.6 mg, 201 μmol, Eq: 1.5) followed by triethylamine (30 μL, 215 μmol, Eq: 1.6) and the resulting solution was stirred at rt for 2 h. The reaction was poured into saturated aqueous NaHCO3 (10 mL) and the mixture was extracted with EtOAc (10 mL). The EtOAc layer was concentrated in vacuo and the crude material was purified by flash chromatography (silica gel, 12 g, 0% to 100% EtOAc in hexanes) to give tert-butyl (2S)-1-((2S)-1-(2-(ethylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (50 mg), m/z=476 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09309248B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-9b759e01eb9d45388128f8f4928e716a |
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| Source note | uspto-grants-2016_04 |
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