Lithium Hydroxide → HCID 24821992, compound

HRID 1675337Notes

Reaction equation

HRID 1675337 reaction equation
[OH-].[Li+].C([N:6]([CH2:15][C@H:16]1[C@H:20]([OH:21])[CH2:19][C@@H:18]([Cl:22])[C@@H:17]1[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([Cl:14])[CH:8]=1)(=O)C>C1COCC1>[Cl:22][C@H:18]1[C@H:17]([CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[C@@H:16]([CH2:15][NH:6][C:7]2[CH:8]=[C:9]([Cl:14])[CH:10]=[C:11]([Cl:13])[CH:12]=2)[C@H:20]([OH:21])[CH2:19]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 24821991HCID 24821991, compound

Product 1

HCID 24821992HCID 24821992, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (21 μL of a 1.0 M aqueous solution, 0.021 mmol) was added to a solution of acetate 10 (2 mg, 0.004 mmol) in THF (0.2 mL). After stirring 3 d at room temperature, the reaction mixture was partitioned between aqueous HCl (1.0 N, 2 mL) and EtOAc (2 mL). The phases were separated and the aqueous phase was extracted with EtOAc (2 mL). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford 1 mg (55%) of the title compound (11).

Workup

  1. customthe reaction mixture was partitioned between aqueous HCl (1.0 N, 2 mL) and EtOAc (2 mL)
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (2 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b4ca98587154b8aa88c2d14a5a32125
Source dataset
uspto-grants-2011_08
Patent number
US08003680B2

Reaction notes

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