HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 1,1-dimethylethyl (1S,4S)-5-(3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | (2S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acid | HCID 9899995 | — |
| Reactant | (1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane | HCID 11521263 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1,1-dimethylethyl (1S,4S)-5-(3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate | HCID 67215823 | 100.9% |
Reaction Steps
A mixture of 3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valine (1.55 g, 5.84 mmol), 1,1-dimethylethyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1.1 g, 5.56 mmol), EDC (1.28 g, 111 mmol), HOBt (150 mg, 1.11 mmol), NMM (1.69 g, 16.7 mmol) in CH2Cl2 (20 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and CH2Cl2. The two layers were separated; the organic dried over anhydrous Na2SO4 and concentrated to give the title compound (2.5 g) as a pale yellow solid. LCMS (m/z): 446.2 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08450484B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-86c56571c9ed4f85a185387547788061 |
| Source note | uspto-grants-2013_05 |