Trifluoroacetic acid → HCID 86704074, compound

HRID 2206383Notes

Reaction equation

HRID 2206383 reaction equation
C(OC([NH:8][C@H:9]([CH3:57])[C:10]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:56])[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([C@H:26]2[C@H:30]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:32]=3[F:38])[C@:29]([C:41]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:42]=3[F:48])([C:39]#[N:40])[C@H:28]([CH2:49][C:50]([CH3:53])([CH3:52])[CH3:51])[NH:27]2)=[O:25])=[C:19]([O:54][CH3:55])[CH:18]=1)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@H:9]([CH3:57])[C:10]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:56])[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([C@H:26]2[C@H:30]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:32]=3[F:38])[C@:29]([C:41]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:42]=3[F:48])([C:39]#[N:40])[C@H:28]([CH2:49][C:50]([CH3:52])([CH3:53])[CH3:51])[NH:27]2)=[O:25])=[C:19]([O:54][CH3:55])[CH:18]=1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86704073HCID 86704073, compound

Product 1

HCID 86704074HCID 86704074, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in Example 4, 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 2-((R)-2-tert-butoxycarbonylamino-propionyloxy)-ethyl ester (Example 5, 112 mg, 0.135 mmol) in methylene chloride (2 mL) was treated with trifluoroacetic acid (2 mL) 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 2-((R)-2-amino-propionyloxy)-ethyl ester as a white solid. MS (ES+) m/z calcd. for C36H39Cl2F2N4O6 [(M+H)+]: 731. found: 731.

Sources & evidence

ORD record
ord-04fd1133414e40f7892af1f7b616f50e
Source dataset
uspto-grants-2016_06
Patent number
US09371280B2

Reaction notes

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