HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → Dicyclohexylcarbodiimide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Perindopril | HCID 107807 | — |
| Reactant | (2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid | HCID 10015159 | — |
| Reactant | (2S,3aS,7aS)-2-carboxyperhydroindole, p-toluenesulfonate salt | HCID 131727202 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Dicyclohexylcarbodiimide | HCID 10868 | — |
Reaction Steps
Langlois et. al. in published PCT Appln. No. WO 01/58868 disclose a further method for preparation of the (S,S) diastereoisomer of N-[(S)-1-carbethoxybutyl]-(S)-alanine, a key intermediate for perindopril comprising reacting benzyl ester of (2S, 3aS,7aS)-2-carboxyperhydroindole, p-toluenesulfonate salt with (S,S) diastereoisomer of N-[(S)-1-carbethoxybutyl]-(S)-alanine in the presence of 0.4 to 0.6 moles of 1-hydroxybenzotriazole; 1 to 1.2 moles of dicyclohexylcarbodiimide and I mole of triethylamine at 77° C. to give the dipeptide compound, which on debenzylation gives perindopril.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07521566B2 |
| Source dataset | uspto-grants-2009_04 |
| ORD ID | ord-8e71a438f5384b94a9c5e9bb704a4294 |
| Source note | uspto-grants-2009_04 |