Lithium hydroxide, monohydrate → HCID 60133249, compound

HRID 628806Notes

Reaction equation

HRID 628806 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:26][CH:27]=[CH2:28])[CH:9]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19]CCCC)=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:26][CH:27]=[CH2:28])[C@@H:9]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:24][CH:25]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86619549HCID 86619549, compound

Product 1

HCID 60133249HCID 60133249, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A THF/MeOH/water (8 ml/8 ml/3 ml) solution containing the intermediate from Step F (790 mg, 1.98 mmol) and lithium hydroxide monohydrate (406 mg, 9.90 mmol) was stirred overnight at room temperature. The solution was concentrated and the nonvolatile portion was partitioned between aqueous 2N hydrochloric acid and EtOAc. The organic phase was dried over Na2SO4, filtered and concentrated to give the title compound. 1H NMR (500 MHz, DMSO-d6): δ 7.90 (d, J=8.2 Hz, 2H); 7.39 (d, J=8.5 Hz, 2H); 7.36 (d, J=8.5 Hz, 2H); 7.26 (d, J=8.4 Hz, 2H); 5.36-5.26 (m, 1H); 4.71-4.60 (m, 2H); 2.94-2.84 (m, 2H); 2.13-2.07 (m, 1H); 1.95-1.87 (m, 1H); 1.42-1.34 (m, 1H); 1.19-1.11 (m, 1H); 0.85-0.77 (m, 2H); 0.60 (t, J=7.3 Hz, 3H). LC3 2.57 min (M+H) 343

Workup

  1. concentrationThe solution was concentrated
  2. customthe nonvolatile portion was partitioned between aqueous 2N hydrochloric acid and EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ce7a78c871754101ad83a35602fb08dd
Source dataset
uspto-grants-2016_04
Patent number
US09315457B2

Reaction notes

Loading…