HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → tert-Butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(1S,2S)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]amino}-3-oxopropyl]pyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | (1S,2S)-1-((tert-Butoxycarbonyl)amino)-2-phenylcyclopropanecarboxylic acid | HCID 7009514 | — |
| Reactant | (3R,4S,5S)-tert-butyl 4-((S)-2-(((benzyloxy)carbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate | HCID 10529182 | — |
| Reactant | tert-Butyl[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylpropan-2-yl]carbamate | HCID 89181604 | — |
| Product | tert-Butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(1S,2S)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]amino}-3-oxopropyl]pyrrolidine-1-carboxylate | HCID 89496847 | — |
Reaction Steps
The title compound was prepared analogously to the synthesis of Intermediates 5 and 6 in three steps by coupling commercially available (1S,2S)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylic acid with 1,2-oxazinane hydrochloride (Starting Material 5), subsequent deprotection with trifluoroacetic acid and another coupling with Starting Material 1. The end product was purified by preparative HPLC.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08722629B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-e1c0f808fa85449b862c5eed6eaf176f |
| Source note | uspto-grants-2014_05 |