Lithium Hydroxide → HCID 67358235, compound

HRID 1667187Notes

Reaction equation

HRID 1667187 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]1=[O:25])C.[OH-].[Li+]>C(O)C.O>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:26])=[O:3])[C:7](=[O:25])[CH:8]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67359102HCID 67359102, compound

Product 1

HCID 67358235HCID 67358235, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a solution of Example 101B (0.77 g, 2.12 mmol) in ethanol/water (1:3, 30 mL) was added lithium hydroxide (0.26 g, 6.37 mmol), and the reaction mixture was stirred at ambient temperature overnight. Then the mixture was concentrated and partitioned in cold 1 N HCl/methylene chloride. The organic layer was separated, dried over MgSO4 and concentrated to yield the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.86 (s, 1H), 7.35 (m, 5H), 5.47 (s, 1H), 4.09 (dd, 2H), 3.90 (d, J=15.26 Hz, 1H), 3.53 (m, 1H), 3.28 (m, 1H), 1.40 (s, 9H); MS/DCI 352 (M+NH4)+.

Workup

  1. concentrationThen the mixture was concentrated
  2. custompartitioned in cold 1 N HCl/methylene chloride
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-07d35442771e4b20bdeec12840dd3783
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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