Hydrochloric Acid → HCID 70925674, compound

HRID 1503275Notes

Reaction equation

HRID 1503275 reaction equation
[CH3:1][N:2]1[C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([C:19]2[N:24]=[CH:23][C:22]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:21][N:20]=2)(C(OCC2C=CC=CC=2)=O)[C:3]1=[O:33].[OH-].[Na+].Cl>C(O)C>[CH3:1][N:2]1[C:6]([CH3:8])([CH3:7])[CH2:5][CH:4]([C:19]2[N:20]=[CH:21][C:22]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:23][N:24]=2)[C:3]1=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70937836HCID 70937836, compound

Product 1

HCID 70925674HCID 70925674, compoundYield 65,493.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (RS)-benzyl 1,5,5-trimethyl-2-oxo-3-(5-(phenylethynyl)pyrimidin-2-yl)pyrrolidine-3-carboxylate (Example 5, step 2) (205 mg, 0.47 μmol) in 3 ml of ethanol was added 1N sodium hydroxide solution (933 μl, 0.94 mmol). After stirring for 1.5 h at room temperature, the pH was neutralized by addition of 1N HCl, and the solvent was evaporated in vaccuo. The residue (165 mg, yellow oil) was loaded onto a 20 g prepacked flash chromatography column. After elution with a 15% to 100% ethyl acetate in heptane gradient, the fractions containing the desired product were collected to yield 94 mg (66%) of the title compound as a light yellow crystalline solid, MS: m/e=306.2 (M+H+).

Workup

  1. customthe solvent was evaporated in vaccuo
  2. washAfter elution with a 15% to 100% ethyl acetate in heptane gradient
  3. additionthe fractions containing the desired product
  4. customwere collected

Sources & evidence

ORD record
ord-00f48c9be833434b976ab4ef447231e5
Source dataset
uspto-grants-2015_12
Patent number
US09212171B2

Reaction notes

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