Lithium Hydroxide → HCID 9862103, compound

HRID 1357495Notes

Reaction equation

HRID 1357495 reaction equation
[OH-].[Li+].[C:3]([NH:6][C@@H:7]1[C@@H:12]([CH2:13][CH:14]2[CH2:16][O:15]2)[CH2:11][C:10]([C:17]([O:19]C)=[O:18])=[CH:9][C@H:8]1[O:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])(=[O:5])[CH3:4]>C1COCC1>[C:3]([NH:6][C@@H:7]1[C@@H:12]([CH2:13][CH:14]2[CH2:16][O:15]2)[CH2:11][C:10]([C:17]([OH:19])=[O:18])=[CH:9][C@H:8]1[O:21][CH:22]([CH2:23][CH3:24])[CH2:25][CH3:26])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 131723972HCID 131723972, compound

Product 1

HCID 9862103HCID 9862103, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous lithium hydroxide solution (0.1N, 15 mL) was added to a room temperature solution of Example 4A (40 mg, 0.118 mmol) in THF (5 mL). The solution was stirred for 10 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 37 mg (96%) 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-ad5359d239e14493b5bac221c17e0324
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

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