Trifluoroacetic acid → Trifluoroacetic acid

HRID 1471186Notes

Reaction equation

HRID 1471186 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[CH3:8][Si:9]([C:12]#[C:13][C:14]1[NH:18][C:17]([C@@H:19]2[CH2:24][C@@H:23]3[C@@H:21]([CH2:22]3)[N:20]2C(OC(C)(C)C)=O)=[N:16][CH:15]=1)([CH3:11])[CH3:10]>ClCCCl>[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[CH3:8][Si:9]([C:12]#[C:13][C:14]1[N:18]=[C:17]([C@@H:19]2[CH2:24][C@@H:23]3[C@@H:21]([CH2:22]3)[NH:20]2)[NH:16][CH:15]=1)([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58498793(1R,3S,5R)-tert-butyl 3-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 178504187HCID 178504187, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

TFA (500 μl, 6.49 mmol) was added to a solution of (1R,3S,5R)-tert-butyl 3-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)-2-azabicyclo[3.1.0]hexane-2-carboxylate (299 mg, 0.865 mmol) in DCE (5 mL) and the reaction was stirred at rt for 30 min. The reaction was concentrated to dryness and then resubmitted to the reaction conditions for 5 h. The reaction was concentrated to yield a TFA salt of (1R,3S,5R)-3-(4-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)-2-azabicyclo[3.1.0]hexane as a viscous brown oil which was used without further purification. LC-MS retention time 2.755 min; m/z 246.25 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 3u C18 2.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 0.8 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where Solvent A was 10% MeOH/90% H2O/0.1% trifluoroacetic acid and Solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a MICROMASS® Platform for LC in electrospray mode.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. customresubmitted to the reaction conditions for 5 h
  3. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-8bddf400e04444f1a7034fa1f3637b94
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Reaction notes

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