HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-tert-Butyl N-((phenylmethoxy)carbonyl)-L-glutamate | HCID 107472 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofurane dichloromethane | HCID 21919333 | — |
| Product | 4-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid butyl ester | HCID 45140359 | — |
Reaction Steps
Cbz-(L)Glu(OtBu)-OH (10 g), HOBT hydrate (5 g), EDCI hydrochloride (6.3 g), intermediate 1.4 (6 g) and DIPEA (10 mL) were dissolved in DCM/THF (1/1, 84 mL). The mixture was stirred at RT for 1 h. DCM and an aq. NaHCO3 solution were added to the mixture and the phases were separated. The org. phase was washed with a 1M NaHSO4 solution, dried (Na2SO4) and evaporated off. CC of the crude (EA/Hept 1/2) offered 13.8 g of the desired compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08288385B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-51d88012dbf54d53990a2407af394703 |
| Source note | uspto-grants-2012_10 |