Lithium Hydroxide → HCID 9883202, compound

HRID 1357497Notes

Reaction equation

HRID 1357497 reaction equation
[OH-].[Li+].[C:3]([NH:6][C@@H:7]1[C@@H:12]([CH2:13][CH:14]=[O:15])[CH2:11][C:10]([C:16]([O:18]C)=[O:17])=[CH:9][C@H:8]1[O:20][CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])(=[O:5])[CH3:4]>C1COCC1>[C:3]([NH:6][C@@H:7]1[C@@H:12]([CH2:13][CH:14]=[O:15])[CH2:11][C:10]([C:16]([OH:18])=[O:17])=[CH:9][C@H:8]1[O:20][CH:21]([CH2:22][CH3:23])[CH2:24][CH3:25])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11723842HCID 11723842, compound

Product 1

HCID 9883202HCID 9883202, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous lithium hydroxide solution (0.1N, 15 mL) was added to a room temperature solution of Example 7A (30 mg, 0.092 mmol) in THF (3 mL). The solution was stirred for 12 hours, acidified to pH 5-6 with DOWEX® 50WX2-200 ion-exchange resin, filtered and concentrated. The concentrate was purified by flash chromatography on silica gel using acetic acid/ethyl acetate (1/5) to afford 23 mg (100%) of the desired product as a white solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-72e15c4a0d054d2b9034fbc031e57197
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

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