Lithium Hydroxide → 880466-44-4

HRID 917316Notes

Reaction equation

HRID 917316 reaction equation
[OH-].[Li+].C([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]3[C:21](=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=4)[N:23]=2)[N:20]=[CH:19][CH:18]=[CH:17]3)[CH2:10][CH2:9]1)=[O:7])C>C1COCC1.CO>[F:30][C:26]1[CH:25]=[C:24]([C:22]2[N:23]=[C:14]([CH:11]3[CH2:10][CH2:9][CH:8]([C:6]([OH:7])=[O:5])[CH2:13][CH2:12]3)[CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69399171HCID 69399171, compound

Product 1

HCID 9924539880466-44-4

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Lithium hydroxide (1M (aq), 24.3 ml, 24.3 mmol) is added to a solution of 4-[8-(3-fluorophenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid ethyl ester (4.60 g, 12.14 mmol) in THF/methanol (40 ml:20 ml) and stirred at room temperature overnight. The organic solvents are removed by evaporation, then the aqueous residue diluted with water and basified to pH9 with 1M KOH. The aqueous layer is then washed with ethyl acetate (3×). The aqueous layer is acidified to pH 4 with 1M HCl to give a white precipitate, which is extracted into ethyl acetate. The ethyl acetate layer is then dried over sodium sulfate, filtered and concentrated to yield the desired product as a yellow foam. Further trituration with 1M HCl yields the product as a pale yellow powder (2.153 g). MS (AP+) 350.6

Workup

  1. customThe organic solvents are removed by evaporation
  2. additionthe aqueous residue diluted with water and basified to pH9 with 1M KOH
  3. washThe aqueous layer is then washed with ethyl acetate (3×)
  4. customto give a white precipitate, which
  5. extractionis extracted into ethyl acetate
  6. dry with materialThe ethyl acetate layer is then dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8ff623813018435ead8a9538cff71815
Source dataset
uspto-grants-2007_09
Patent number
US07273875B2

Reaction notes

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