Trifluoroacetic acid → 4-(2-amino-5-((3R,5S)-5-(methoxycarbonyl)pyrrolidin-3-yl)pyridin-3-yl)-2-fluorobenzoic acid-2TFA

HRID 596107Notes

Reaction equation

HRID 596107 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][N:11](C(OC(C)(C)C)=O)[C@H:10]([C:20]([O:22][CH3:23])=[O:21])[CH2:9]2)=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([O:32]C(C)(C)C)=[O:31])=[C:26]([F:37])[CH:25]=1.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>C(Cl)Cl>[OH:44][C:38]([C:40]([F:43])([F:42])[F:41])=[O:39].[OH:44][C:38]([C:40]([F:43])([F:42])[F:41])=[O:39].[NH2:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([OH:32])=[O:31])=[C:26]([F:37])[CH:25]=2)=[CH:4][C:5]([C@H:8]2[CH2:9][C@@H:10]([C:20]([O:22][CH3:23])=[O:21])[NH:11][CH2:12]2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118045509(2S,4R)-1-tert-butyl 2-methyl 4-(6-amino-5-(4-(tert-butoxycarbonyl)-3-fluorophenyl)pyridin-3-yl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 1317346254-(2-amino-5-((3R,5S)-5-(methoxycarbonyl)pyrrolidin-3-yl)pyridin-3-yl)-2-fluorobenzoic acid-2TFAYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2S,4R)-1-tert-butyl 2-methyl 4-(6-amino-5-(4-(tert-butoxycarbonyl)-3-fluorophenyl)pyridin-3-yl)pyrrolidine-1,2-dicarboxylate (300 mg, 0.58 mmol) in DCM (6 mL) was treated with TFA (3 mL). After 1 h, the reaction was concentrated, then the residue was slurried in benzene, sonicated, then concentrated to provide 4-(2-amino-5-((3R,5S)-5-(methoxycarbonyl)pyrrolidin-3-yl)pyridin-3-yl)-2-fluorobenzoic acid-2TFA (345 mg, 100% yield). LCMS (m/z): 360.2 (MH+), 0.34 min.

Workup

  1. concentrationthe reaction was concentrated
  2. customsonicated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-18ba4d19365142da8e50282ff667eeb3
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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