HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl Alcohol → Benzyl-(1S,2R)-1-({(2R,3R)-3-methoxy-2-methyl-3-[(2S)-pyrrolidin-2-yl]propanoyl}amino)-2-phenylcyclopropanecarboxylate trifluoroacetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Dicyclohexylamine | HCID 7582 | — |
| Reactant | (1S,2R)-N-Boc-1-amino-2-phenylcyclopropanecarboxylic acid | HCID 7009512 | — |
| Reactant | (3R,4S,5S)-tert-butyl 4-((S)-2-(((benzyloxy)carbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate | HCID 10529182 | — |
| Reactant | benzyl (1S,2R)-1-amino-2-phenylcyclopropanecarboxylate | HCID 66837318 | — |
| Product | Benzyl-(1S,2R)-1-({(2R,3R)-3-methoxy-2-methyl-3-[(2S)-pyrrolidin-2-yl]propanoyl}amino)-2-phenylcyclopropanecarboxylate trifluoroacetate | HCID 70979740 | — |
Reaction Steps
The title compound was prepared in analogy to the synthesis of Intermediate 18, proceeding from (2R,3R)-3-[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-3-methoxy-2-methylpropanoic acid (Starting Compound 1), which was released from the dicyclohexylamine salt, and benzyl(1S,2R)-1-amino-2-phenylcyclopropanecarboxylate. Benzyl (1S,2R)-1-amino-2-phenylcyclopropanecarboxylate had been prepared beforehand by standard methods, by esterifying commercially available (1S,2R)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylic acid with benzyl alcohol and subsequent Boc detachment with trifluoroacetic acid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08992932B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-028cbfe4ed1f485d93568a6bae8bd703 |
| Source note | uspto-grants-2015_03 |