Lithium hydroxide, monohydrate → HCID 72195898, compound

HRID 626351Notes

Reaction equation

HRID 626351 reaction equation
[CH3:1][N:2]([CH3:38])[C:3]([O:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[C:14]([C:22]([NH:24][C:25]3[CH:26]=[C:27](/[CH:31]=[CH:32]/[C:33]([O:35]CC)=[O:34])[CH:28]=[CH:29][CH:30]=3)=[O:23])[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=[CH:10][CH:11]=1)=[O:4].O[Li].O>C1COCC1.O>[CH3:38][N:2]([CH3:1])[C:3]([O:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[C:14]([C:22]([NH:24][C:25]3[CH:26]=[C:27](/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34])[CH:28]=[CH:29][CH:30]=3)=[O:23])[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=[CH:10][CH:11]=1)=[O:4]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 117951687HCID 117951687, compound

Product 1

HCID 72195898HCID 72195898, compoundYield 66%

Reagents, catalysts & solvents 1

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

Procedure

Compound 26 (0.23 mmol,) was dissolved in THF/H2O (1:1, 20 mL) mixture. LiOH.H2O (0.35 mmol,) was added to the reaction mixture and stirred at room temperature for 3 h. The reaction mixture was concentrated under vacuum to dryness. The resulting residue was adjusted to pH 5 with dilute HCl and extracted with ethyl acetate (3×10 mL), washed with water and brine. The organic layer was dried over Na2SO4, filtered, and the solvent was removed in vacuo. The resulting solid was purified using reverse phase column chromatography to afford pure 27 as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum to dryness
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe resulting solid was purified

Sources & evidence

ORD record
ord-d5bea0043fc842a58617e6988c90f94f
Source dataset
uspto-grants-2016_04
Patent number
US09309187B2

Reaction notes

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