Lithium hydroxide, monohydrate → HCID 59778157, compound

HRID 1643882Notes

Reaction equation

HRID 1643882 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=2)[CH2:11][CH:10]([C:22]([O:24]CC)=[O:23])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>CO.C1COCC1.O>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([F:19])([F:20])[F:21])=[CH:15][CH:16]=2)[CH2:11][CH:10]([C:22]([OH:24])=[O:23])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59778148HCID 59778148, compound

Product 1

HCID 59778157HCID 59778157, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 149C (825 mg, 2.27 mmol) in a mixed solvent of MeOH-THF-H2O (20 mL at ratio of 2:2:1) was added lithium hydroxide monohydrate (400 mg, 11.35 mmol). The mixture was stirred at RT for 2 h, then extracted with ether (20 mL). The aqueous layer was acidified to pH 4-5 using 3N aqueous HCl, then extracted with CH2Cl2 (3×). The combined CH2Cl2 extracts were washed with water, brine, dried (Na2SO4), and concentrated in vacuo to afford compound 149D as light yellow foam (735 mg, 97%).

Workup

  1. extractionextracted with ether (20 mL)
  2. extractionextracted with CH2Cl2 (3×)
  3. washThe combined CH2Cl2 extracts were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86b6b0a4a2a94033b2ba449933786ed1
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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