Lithium Hydroxide → HCID 59218448, compound

HRID 2246679Notes

Reaction equation

HRID 2246679 reaction equation
[F:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([C:26]2[N:30]([CH3:31])[CH:29]=[N:28][N:27]=2)[CH2:21][C:22]([O:24]C)=[O:23])=[CH:16][CH:15]=1.[Li+].[OH-]>C1COCC1.CCO>[F:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([C:26]2[N:30]([CH3:31])[CH:29]=[N:28][N:27]=2)[CH2:21][C:22]([OH:24])=[O:23])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59218440HCID 59218440, compound

Product 1

HCID 59218448HCID 59218448, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution of 47.9 (100 mg, 0.24 mmol) in THF/EtOH (6 mL, 3/1, v/v) is 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 47.

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 47

Sources & evidence

ORD record
ord-0752133ba23f4cd8938ee8c88fa816bf
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

Loading…