Potassium Carbonate → HCID 58498696, compound

HRID 1471188Notes

Reaction equation

HRID 1471188 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][CH:8]([CH3:34])[C@H:9]([NH:29][C:30](=[O:33])[O:31][CH3:32])[C:10](=[O:28])[N:11]1[C@H:16]([C:17]2[NH:18][C:19]([C:22]#[C:23][Si](C)(C)C)=[CH:20][N:21]=2)[CH2:15][C@@H:14]2[C@H:12]1[CH2:13]2>CO>[C:22]([C:19]1[NH:18][C:17]([C@@H:16]2[CH2:15][C@@H:14]3[C@@H:12]([CH2:13]3)[N:11]2[C:10](=[O:28])[C@@H:9]([NH:29][C:30](=[O:33])[O:31][CH3:32])[CH:8]([CH3:34])[CH3:7])=[N:21][CH:20]=1)#[CH:23]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58498865HCID 58498865, compound

Product 1

HCID 58498696HCID 58498696, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Potassium carbonate (34.3 mg, 0.248 mmol) was added to a solution of methyl(S)-3-methyl-1-oxo-1-((1R,3S,5R)-3-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)-2-azabicyclo[3.1.0]hexan-2-yl)butan-2-ylcarbamate (200 mg, 0.497 mmol) in methanol (5 mL) and the reaction was flushed with nitrogen, sealed and then heated at 50° C. for 4 h. and then stirred at rt overnight. The reaction was concentrated to dryness and then purified on a BIOTAGE® Horizon (12 g SiO2, 70-90% EtOAc/hexanes) to yield methyl(S)-1-((1R,3S,5R)-3-(5-ethynyl-1H-imidazol-2-yl)-2-azabicyclo[3.1.0]hexan-2-yl)-3-methyl-1-oxobutan-2-ylcarbamate (151 mg) as a yellow glass. LC-MS retention time 1.788 min; m/z 331.32 (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. customthe reaction was flushed with nitrogen
  2. customsealed
  3. concentrationThe reaction was concentrated to dryness
  4. custompurified on a BIOTAGE® Horizon (12 g SiO2, 70-90% EtOAc/hexanes)

Sources & evidence

ORD record
ord-65f3caa98c6f4463a924eb842a4ce0c1
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Reaction notes

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