Cesium carbonate → HCID 86696312, compound

HRID 882383Notes

Reaction equation

HRID 882383 reaction equation
Cl[CH2:2][O:3][C:4]([NH:6][C@@H:7]([CH3:18])[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:5].N[C@@H](C)C(OCC1C=CC=CC=1)=O.ClC(OCCl)=O.[Cl:38][C:39]1[C:40]([F:79])=[C:41]([C@@H:45]2[C@:49]([C:52]3[CH:57]=[CH:56][C:55]([Cl:58])=[CH:54][C:53]=3[F:59])([C:50]#[N:51])[C@H:48]([CH2:60][C:61]([CH3:64])([CH3:63])[CH3:62])[NH:47][C@H:46]2[C:65]([NH:67][C:68]2[CH:76]=[CH:75][C:71]([C:72]([OH:74])=[O:73])=[CH:70][C:69]=2[O:77][CH3:78])=[O:66])[CH:42]=[CH:43][CH:44]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl.CN(C)C=O.N1C=CC=CC=1>[Cl:38][C:39]1[C:40]([F:79])=[C:41]([C@@H:45]2[C@:49]([C:52]3[CH:57]=[CH:56][C:55]([Cl:58])=[CH:54][C:53]=3[F:59])([C:50]#[N:51])[C@H:48]([CH2:60][C:61]([CH3:63])([CH3:64])[CH3:62])[NH:47][C@H:46]2[C:65]([NH:67][C:68]2[CH:76]=[CH:75][C:71]([C:72]([O:74][CH2:2][O:3][C:4](=[O:5])[NH:6][C@@H:7]([CH3:18])[C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])=[O:73])=[CH:70][C:69]=2[O:77][CH3:78])=[O:66])[CH:42]=[CH:43][CH:44]=1

Participants

9

Reactant 5

HCID 10796Cesium carbonateHCID 62754Chloromethyl chloroformateHCID 726858benzyl (2S)-2-aminopropanoateHCID 53358942IdasanutlinHCID 69430934HCID 69430934, compound

Product 1

HCID 86696312HCID 86696312, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in Example 23, (S)-benzyl 2-((chloromethoxy)-carbonylamino)propanoate was prepared from (S)-benzyl 2-aminopropanoate (Chem-Impex) and 1-chloromethyl chloroformate (Aldrich) in the presence of pyridine in methylene chloride. It was then reacted with chiral 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoic acid and cesium carbonate in dimethylformamide to give 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 as a white solid.

Sources & evidence

ORD record
ord-2db688af3dcb4686955353303abc31f9
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

Loading…