HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → {(S)-1-[(S)-1-(5-Bromo-2-methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | (S)-3-amino-1-(5-bromo-2-methoxy-naphthalen-1-ylmethyl)-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one trifluoroacetate | HCID 118677404 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | {(S)-1-[(S)-1-(5-Bromo-2-methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester | HCID 90220831 | 95.8% |
Reaction Steps
Boc-N-Me-Ala-OH (107.91 mg, 0.532 mmol), DIPEA (0.251 mL, 1.45 mmol) and HATU (220.37 mg, 0.58 mmol) were added to a solution of (S)-3-amino-1-(5-bromo-2-methoxy-naphthalen-1-ylmethyl)-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one trifluoroacetate (260 mg) in DMF (4 mL) at 0° C. After 3 h the mixture was diluted with water and extracted with ethyl acetate. The extracts were washed with 1 M aqueous citric acid solution, brine, saturated aqueous sodium carbonate solution, dried and concentrated. The residue was purified by silica gel chromatography to afford the title compound (282 mg, 51%) as an off white solid. LC-MS: 613.2 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409888B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-56040588c61f4e719e35579a8c51f87a |
| Source note | uspto-grants-2016_08 |