HCID 86696309, compound → HCID 71738132, compound

HRID 882375Notes

Reaction equation

HRID 882375 reaction equation
C(OC(C[CH:12]([O:17][C:18](=[O:58])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([C@H:28]2[C@H:32]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=3[F:40])[C@:31]([C:43]3[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][C:44]=3[F:50])([C:41]#[N:42])[C@H:30]([CH2:51][C:52]([CH3:55])([CH3:54])[CH3:53])[NH:29]2)=[O:27])=[C:21]([O:56][CH3:57])[CH:20]=1)[O:13][C:14](=[O:16])[NH2:15])=O)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[Cl:39][C:35]1[C:34]([F:40])=[C:33]([C@@H:32]2[C@:31]([C:43]3[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][C:44]=3[F:50])([C:41]#[N:42])[C@H:30]([CH2:51][C:52]([CH3:55])([CH3:53])[CH3:54])[NH:29][C@H:28]2[C:26]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([C:18]([O:17][CH2:12][O:13][C:14]([NH:15][CH2:19][C:18]([OH:58])=[O:17])=[O:16])=[O:58])=[CH:20][C:21]=2[O:56][CH3:57])=[O:27])[CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 2

HCID 86696309HCID 86696309, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71738132HCID 71738132, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a manner similar to the method described in Example 24, a solution of 4-{[(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-3-methoxy-benzoic acid benzyloxycarbonylmethyl-carbamoyloxymethyl ester (Example 29) in ethyl acetate was treated with 10% palladium on carbon under 1 atm of hydrogen to give 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)acetic acid as a white solid. MS (ES+) m/z calcd. for C35H36Cl2F2N4O8 [(M+H)+]: 747, found: 747.

Sources & evidence

ORD record
ord-56abb4e0b55f4c4b9a227d6b066b3576
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

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