Lithium Hydroxide → HCID 6971045, compound

HRID 276099Notes

Reaction equation

HRID 276099 reaction equation
[Li+].[OH-].[C:3]([NH:6][C@@H:7]1[C@H:16]([O:17]C(=O)C)[C@@H:15]([O:21]C(=O)C)[C@H:14]([CH2:25][O:26]C(=O)C)[O:13][C@@H:8]1[O:9]C(=O)C)(=[O:5])[CH3:4]>C1COCC1.O>[C:3]([NH:6][C@@H:7]1[C@H:16]([OH:17])[C@@H:15]([OH:21])[C@H:14]([CH2:25][OH:26])[O:13][C@@H:8]1[OH:9])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 26470288HCID 26470288, compound

Product 1

HCID 6971045HCID 6971045, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of aqueous LiOH (0.3M, 20 mL) was added dropwise to a solution containing Compound 10 (0.52 g, 1.34 mmol) in THF-H2O (3:1, 22 mL). From TLC, the reaction was complete within 30 minutes. Dowex® 50W-X8[H+] was added to neutralize the solution, then the resin was filtered off, and the filtrate was concentrated. The product was purified by flash column chromatography with CHCl3—MeOH (3.5:1) to obtain 0.29 g (1.3 mmol) of Compound 11 (97 percent yield). Further purification was carried out with Bio Gel P-2 chromatography using water as eluent.

Workup

  1. additionDowex® 50W-X8[H+] was added
  2. filtrationthe resin was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe product was purified by flash column chromatography with CHCl3—MeOH (3.5:1)

Sources & evidence

ORD record
ord-a4f300ddadc4421ebc885534f1b68fb5
Source dataset
uspto-grants-2002_03
Patent number
US06353095B1

Reaction notes

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