Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Isobutyryl chloride | HCID 62325 | — |
| Reactant | Methyl (S)-3-tert-butoxycarbonylamino-2-piperazin-1-ylpropanoate | HCID 86675027 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86675028 | HCID 86675028 | 81.1% |
Reaction Steps
1.2 ml (8.3 mmol) of triethylamine and then 0.8 ml (7.6 mmol) of isobutyryl chloride are added to a solution of 2.0 g (6.9 mmol) of methyl (S)-3-tert-butoxycarbonylamino-2-piperazin-1-ylpropanoate in 20 ml of dichloromethane, cooled beforehand to 0° C. After stirring at ambient temperature for 1 h 30, water is added. The reaction medium is extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude residue obtained is purified by chromatography on silica gel, elution being carried out with a 50/50 heptane/ethyl acetate mixture. 2.0 g (81%) of methyl (S)-3-tert-butoxycarbonylamino-2-(4-isobutyrylpiperazin-1-yl)propanoate are obtained in the form of a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08633196B2 |
|---|
| Source dataset | uspto-grants-2014_01 |
|---|
| ORD ID | ord-45e3a153182b4d0f87babbc0270eb25a |
|---|
| Source note | uspto-grants-2014_01 |
|---|