HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (1R,2R,4S)-2-((S)-1-tert-Butoxycarbonyl-butylcarbamoyl)-4-hydroxy-cyclopentanecarboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | L-norvaline t-butyl ester | HCID 12085932 | — |
| Reactant | 3-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carboxylic acid methyl ester | HCID 59204176 | — |
| Reactant | HCID 178516071 | HCID 178516071 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (1R,2R,4S)-2-((S)-1-tert-Butoxycarbonyl-butylcarbamoyl)-4-hydroxy-cyclopentanecarboxylic acid methyl ester | HCID 59204201 | 96% |
Reaction Steps
Compound 41 (263 mg, 1.55 mmol) and H-Nva-OtBu (420 mg, 2.42 mmol) were dissolved in dry THF (20 mL). DIEA (530 uL, 3.04 mmol) and 2-hydroxypyridine (260 mg, 2.73 mmol) were added and the mixture was refluxed for five days. The solvent was evaporated and the crude product was purified by flash column chromatography (toluene/EtOAc 1:2) to give 42 (510 mg, 96%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07671032B2 |
| Source dataset | uspto-grants-2010_03 |
| ORD ID | ord-5b184a53ff8942a4a032557eedd603f0 |
| Source note | uspto-grants-2010_03 |