Lithium Hydroxide → HCID 66701982, compound

HRID 729689Notes

Reaction equation

HRID 729689 reaction equation
[OH-].[Li+].[CH2:3]([S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([C:21]2[O:25][C:24]([C:26]([O:28]C)=[O:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:14]=[C:13]([NH:30][C@H:31]([CH3:41])[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1.O>[CH2:3]([S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([C:21]2[O:25][C:24]([C:26]([OH:28])=[O:27])=[CH:23][CH:22]=2)(=[O:19])=[O:20])[CH:14]=[C:13]([NH:30][C@H:31]([CH3:41])[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:35])[CH3:36])[N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66702076HCID 66702076, compound

Product 1

HCID 66701982HCID 66701982, compound

Reagents, catalysts & solvents 1

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

Procedure

Lithium hydroxide (33 mg) was added to a solution of the subtitle product of step i) (0.23 g) in THF/H2O (1 ml/1 ml) and stirring maintained for 1 h. The THF was removed in vacuo and the residue neutralised with AcOH before extracting with EtOAc. The organics were then washed with H2O, dried (MgSO4) and concentrated in vacuo. The residue was purified by reverse phase HPLC (gradient 95% to 20% 0.02M ammonium hydroxide/acetonitrile) to yield the title compound as an off-white solid. Yield: 0.14 g.

Workup

  1. temperaturemaintained for 1 h
  2. customThe THF was removed in vacuo
  3. extractionbefore extracting with EtOAc
  4. washThe organics were then washed with H2O
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase HPLC (gradient 95% to 20% 0.02M ammonium hydroxide/acetonitrile)

Sources & evidence

ORD record
ord-11320d807d8c479289c25dbd247b6038
Source dataset
uspto-grants-2009_09
Patent number
US07582644B2

Reaction notes

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