HCID 86696312, compound → HCID 71738357, compound

HRID 882384Notes

Reaction equation

HRID 882384 reaction equation
[Cl:1][C:2]1[C:3]([F:59])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:56]=[CH:55][C:34]([C:35]([O:37][CH2:38][O:39][C:40](=[O:54])[NH:41][C@@H:42]([CH3:53])[C:43]([O:45]CC3C=CC=CC=3)=[O:44])=[O:36])=[CH:33][C:32]=2[O:57][CH3:58])=[O:29])[CH:5]=[CH:6][CH:7]=1.[H][H]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[C:3]([F:59])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:25])([CH3:27])[CH3:26])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:56]=[CH:55][C:34]([C:35]([O:37][CH2:38][O:39][C:40]([NH:41][C@@H:42]([CH3:53])[C:43]([OH:45])=[O:44])=[O:54])=[O:36])=[CH:33][C:32]=2[O:57][CH3:58])=[O:29])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 86696312HCID 86696312, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71738357HCID 71738357, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a manner similar to the method described in Example 24, a solution of chiral ((S)-1-(benzyloxy)-1-oxopropan-2-ylcarbamoyloxy)methyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate 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)propanoic acid as a white solid. MS (ES+) m/z calcd. for C36H36Cl2F2N4O8: [(M+H)+]: 761, found: 761.

Sources & evidence

ORD record
ord-b86fe8c82375450984fd2b305a81ed8b
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

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