Lithium Hydroxide → HCID 59218430, compound

HRID 2246675Notes

Reaction equation

HRID 2246675 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1[C@H:7]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:30]=[C:29]([CH3:31])[C:28]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=3[CH:22]=2)=[CH:15][CH:14]=1)[CH2:8][C:9]([O:11]C)=[O:10].[Li+].[OH-]>C1COCC1.CCO>[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1[C@H:7]([C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]2[CH:30]=[C:29]([CH3:31])[C:28]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=3[CH:22]=2)=[CH:17][CH:18]=1)[CH2:8][C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59218391HCID 59218391, compound

Product 1

HCID 59218430HCID 59218430, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution of 46.7 (150 mg, 3.6 mmol) in THF/EtOH (6 mL, 3/1, v/v) was added 1N LiOH (aq) (2 mL). The reaction mixture is stirred at 23° C. until TLC confirms consumption of the starting material. The organic solvent is removed in vacuo. 1N HCl is added to neutralize the mixture to pH 7. The mixture is extracted with EtOAc (2×10 mL), concentrated in vacuo. The residue is purified by column chromatography (silica, MeOH/DCM), to afford acid 46.

Workup

  1. customconsumption of the starting material
  2. customThe organic solvent is removed in vacuo
  3. addition1N HCl is added
  4. extractionThe mixture is extracted with EtOAc (2×10 mL)
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography (silica, MeOH/DCM)
  7. customto afford acid 46

Sources & evidence

ORD record
ord-e465e6a3b2a445d38e3dd1b5e8f55fdf
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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