Trifluoroacetic acid → Trifluoroacetic acid

HRID 625878Notes

Reaction equation

HRID 625878 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[Br:8][C:9]1[C:10]([O:19][C@H:20]2[CH2:24][N:23](C(OC(C)(C)C)=O)[C@H:22]([C:32]([OH:34])=[O:33])[CH2:21]2)=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2>C(Cl)Cl>[Br:8][C:9]1[C:10]([O:19][C@H:20]2[CH2:24][NH:23][C@H:22]([C:32]([OH:34])=[O:33])[CH2:21]2)=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90457443HCID 90457443, compound

Product 2

HCID 6422Trifluoroacetic acidYield 396.3%HCID 90456612HCID 90456612, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5.0 ml, 65 mmol) was added to a solution of (2S,4R)-4-((3-bromoquinolin-2-yl)oxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (300 mg, 0.686 mmol) in DCM (5 mL) and stirred at RT until LCMS analysis indicated complete conversion. The solution was concentrated to afford the product (2S,4R)-4-((3-bromoquinolin-2-yl)oxy)pyrrolidine-2-carboxylic acid, TFA (310 mg) as a sticky oil. Yield was assumed to be 100%. ESI-MS(+) m/z=337 (M+H).

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-e20b9fa0c7354eb8a06a28868badc6cf
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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