Lithium Hydroxide → HCID 21048953, compound

HRID 2212378Notes

Reaction equation

HRID 2212378 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:28]3[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=3[F:35])[CH2:16][CH2:15][CH:14]([O:17][S:18]([NH:21][CH2:22][CH2:23][O:24]C(=O)C)(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Li+].C(OCC)(=O)C>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:28]3[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=3[F:35])[CH2:12][CH2:13][CH:14]([O:17][S:18](=[O:19])(=[O:20])[NH:21][CH2:22][CH2:23][OH:24])[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 21048966HCID 21048966, compound

Product 1

HCID 21048953HCID 21048953, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product from Example 116 (54 mg, 0.1 mmol) in tetrahydrofuran (2 mL) was added lithium hydroxide (35 mg, 1.5 mmol) in water (2 mL) and the mixture stirred for 2 hours. Ethyl acetate (20 mL) was added, the solution washed with saturated aqueous ammonium chloride (10 mL), saturated aqueous sodium bicarbonate (10 mL) and brine (20 mL), dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography on silica eluting with ethyl acetate:iso-hexane 1:1, to afford the title compound. (33 mg).

Workup

  1. washthe solution washed with saturated aqueous ammonium chloride (10 mL), saturated aqueous sodium bicarbonate (10 mL) and brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto leave a residue which
  5. customwas purified by column chromatography on silica eluting with ethyl acetate:iso-hexane 1:1

Sources & evidence

ORD record
ord-4c9da81958ac4bc3bb2ce4ffd0c2f20c
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

Loading…