Cesium carbonate → HCID 86696309, compound

HRID 882374Notes

Reaction equation

HRID 882374 reaction equation
C(OC(=O)C[NH:11][C:12]([O:14][CH2:15]Cl)=[O:13])C1C=CC=CC=1.[CH2:18]([O:25][C:26](=[O:29])[CH2:27]N)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.ClC(OC(Cl)C)=O.[Cl:37][C:38]1[C:39]([F:78])=[C:40]([C@@H:44]2[C@:48]([C:51]3[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][C:52]=3[F:58])([C:49]#[N:50])[C@H:47]([CH2:59][C:60]([CH3:63])([CH3:62])[CH3:61])[NH:46][C@H:45]2[C:64]([NH:66][C:67]2[CH:75]=[CH:74][C:70]([C:71]([OH:73])=[O:72])=[CH:69][C:68]=2[O:76][CH3:77])=[O:65])[CH:41]=[CH:42][CH:43]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl.CN(C)C=O.N1C=CC=CC=1>[CH2:18]([O:25][C:26]([CH2:27][CH:15]([O:72][C:71](=[O:73])[C:70]1[CH:74]=[CH:75][C:67]([NH:66][C:64]([C@H:45]2[C@H:44]([C:40]3[CH:41]=[CH:42][CH:43]=[C:38]([Cl:37])[C:39]=3[F:78])[C@:48]([C:51]3[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][C:52]=3[F:58])([C:49]#[N:50])[C@H:47]([CH2:59][C:60]([CH3:62])([CH3:63])[CH3:61])[NH:46]2)=[O:65])=[C:68]([O:76][CH3:77])[CH:69]=1)[O:14][C:12](=[O:13])[NH2:11])=[O:29])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 5

HCID 10796Cesium carbonateHCID 409140Benzyl glycinateHCID 5213051-Chloroethyl chloroformateHCID 53358942IdasanutlinHCID 57826258HCID 57826258, compound

Product 1

HCID 86696309HCID 86696309, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in Example 23, chloromethoxycarbonylamino-acetic acid benzyl ester was prepared from amino-acetic acid benzyl ester and 1-chloroethyl 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 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 as a white solid. MS (ES+) m/z calcd. for C42H41Cl2F2N4O8 [(M+H)+]: 837, found: 837

Sources & evidence

ORD record
ord-ee4a510ae6a34fe69f874166ffbce28e
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

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