Lithium Hydroxide → HCID 178524949, compound

HRID 1053628Notes

Reaction equation

HRID 1053628 reaction equation
[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH2:10][C:11]1[C:12]([C:16]([O:18]CC)=[O:17])=[N:13][NH:14][CH:15]=1.[Li+].[OH-].C(OCC)(=O)C>C1COCC1.O>[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH2:10][C:11]1[C:12]([C:16]([OH:18])=[O:17])=[N:13][NH:14][CH:15]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 178470491HCID 178470491, compound

Product 1

HCID 178524949HCID 178524949, compoundYield 113.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of product (1-A) (1.34 g, 3.8 mmol) in THF (30 mL) was added drop-wise a solution of LiOH (0.24 g, 10 mmol) in H2O (30 mL) at 0° C. The reaction mixture was stirred at 50° C. for about 2 h. After cooling, ethyl acetate (20 mL) and H2O (20 mL) were added to the solution. The aqueous layer was separated and acidified with citric acid (to pH=5) and extracted with ethyl acetate (50 mL×3). The combined organic phases were dried over Na2SO4 and concentrated to give crude product (2-A) (1.4 g, 100%) as a light yellow solid. LC-MS (M+H)+=324.

Workup

  1. temperatureAfter cooling
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-67946c946a9940d8b9635e71289c7dae
Source dataset
uspto-grants-2016_07
Patent number
US09394256B2

Reaction notes

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