HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclohexanemethylamine → (1r,2s)-1-{[(2s,4r)-1-[(1S)-1-(cyclohexylmethyl-carbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclohexanemethylamine | HCID 76688 | — |
| Reactant | (S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid | HCID 2734668 | — |
| Reactant | 2-{[(Tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid | HCID 5046859 | — |
| Reactant | Chlorocarbamate | HCID 22035886 | — |
| Reactant | [1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propyl]-carbamic acid tert.butyl ester | HCID 68488177 | — |
| Reactant | 1-{[1-[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester | HCID 68491628 | — |
| Product | (1r,2s)-1-{[(2s,4r)-1-[(1S)-1-(cyclohexylmethyl-carbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid | HCID 68494906 | — |
Reaction Steps
N-(tert-butoxycarbonyl)-L-tert-butylglycine was attached to the resin as described for the preparation of compound 16 followed by reaction with cyclohexanemethylamine as described for the preparation of 17 and removal of the Boc group as described for 18. The afforded compound was then reacted with the chlorocarbamate achieved from 12 as described for the preparation of 13 which gave the title compound. Purity by HPLC>95%. M+H+726.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07608590B2 |
| Source dataset | uspto-grants-2009_10 |
| ORD ID | ord-0a0ba1b1b8a84f909093d6ff1ce3b5a9 |
| Source note | uspto-grants-2009_10 |