HuagongsheHuagongshe Chemistry Print Report · For research reference only
(S)-dibenzyl 2-(((4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoyloxy)methoxy)carbonylamino)-pentanedioate → (S)-2-(((4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoyloxy)methoxy)carbonylamino)-pentanedioic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (S)-dibenzyl 2-(((4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoyloxy)methoxy)carbonylamino)-pentanedioate | HCID 71738207 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (S)-2-(((4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoyloxy)methoxy)carbonylamino)-pentanedioic acid | HCID 71738208 | — |
Reaction Steps
In a manner similar to the method described in Example 24, a solution of chiral (S)-dibenzyl 2-(((4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoyloxy)methoxy)carbonylamino)pentanedioate (Example 31) in ethyl acetate was treated with 10% palladium on carbon under 1 atm of hydrogen to give chiral (S)-2-(((4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoyloxy)methoxy)carbonylamino)-pentanedioic acid as a white solid. MS (ES+) m/z calcd. for C38H39Cl2F2N4O10 [(M+H)+]: 819, found: 819.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08993614B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-0c30e614a77d4d128b1b9bfa51faa551 |
| Source note | uspto-grants-2015_03 |