Lithium Hydroxide → HCID 67484028, compound

HRID 1936269Notes

Reaction equation

HRID 1936269 reaction equation
C[O:2][C:3](=[O:25])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][C:19]2[CH:20]=[N:21][CH:22]=[N:23][CH:24]=2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.O1CCCC1.[OH-].[Li+]>CO.O>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[C:18][C:19]3[CH:20]=[N:21][CH:22]=[N:23][CH:24]=3)=[CH:13][CH:12]=2)[C:3]([OH:25])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 8028TetrahydrofuranHCID 67483971HCID 67483971, compound

Product 1

HCID 67484028HCID 67484028, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-pyrimidin-5-ylethynyl-phenyl)-propionic acid methyl ester (440 mg, 1.32 mmol) in methanol (3 mL), water (2 mL), and tetrahydrofuran (0.5 mL) was treated with lithium hydroxide (38 mg, 0.90 mmol). The reaction mixture was stirred at 25° C. for 60 h. At this time, additional lithium hydroxide (38 mg, 0.90 mmol) was added. The reaction was stirred at 25° C. for 4 h. At this time, the reaction was diluted with water (5 mL) and then concentrated in vacuo. The resulting aqueous layers were washed with ethyl acetate (2×10 mL), acidified with a 1N aqueous hydrochloric acid solution, and then extracted with ethyl acetate (2×25 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-(4-pyrimidin-5-ylethynyl-phenyl)-propionic acid (390 mg, 92%) as an amber foam: EI-HRMS m/e calcd for C20H20N2O2 (M+) 320.1524, found 320.1526.

Workup

  1. stirringThe reaction was stirred at 25° C. for 4 h
  2. concentrationconcentrated in vacuo
  3. washThe resulting aqueous layers were washed with ethyl acetate (2×10 mL)
  4. extractionextracted with ethyl acetate (2×25 mL)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb3f388dbd42413ab4af7076e3b83e5f
Source dataset
uspto-grants-2002_05
Patent number
US06388071B2

Reaction notes

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