Lithium hydroxide, monohydrate → HCID 67496229, compound

HRID 1628272Notes

Reaction equation

HRID 1628272 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:21][C:22]1[N:23]=[CH:24][S:25][CH:26]=1)[C@H:9]([C:17]([O:19]C)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O>C1COCC1.O>[C:1]([O:5][C:6]([N:8]([CH2:21][C:22]1[N:23]=[CH:24][S:25][CH:26]=1)[C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67497661HCID 67497661, compound

Product 1

HCID 67496229HCID 67496229, compoundYield 83.1%

Reagents, catalysts & solvents 1

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

Procedure

Ester 34.8.D (2.75 g, 7.3 mmol) was dissolved in THF/H2O. LiOH hydrate (646 mg, 15.4 mmol) was added and the mixture was stirred at room temperature. The THF was removed on a rotavap and the resulting aqueous layer was acidified with 1.0 N HCl and then conc. HCl. A white sticky solid formed which was extracted with EtOAc. The organic layers were dried with sodium sulfate, filtered, and concentrated to yield 34.8.E as a sticky foam (2.20 g).

Workup

  1. customThe THF was removed on a rotavap
  2. customA white sticky solid formed which
  3. extractionwas extracted with EtOAc
  4. dry with materialThe organic layers were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d2b84c15db04503b67c403a787f237f
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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