Sodium Hydroxide → DG 051 (HCl salt)

HRID 1909642Notes

Reaction equation

HRID 1909642 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1.[OH-].[Na+]>CO>[ClH:27].[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][C@@H:8]3[CH2:9][CH2:10][CH2:11][N:7]3[CH2:6][CH2:5][CH2:4][C:3]([OH:28])=[O:2])=[CH:15][CH:16]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44819339HCID 44819339, compound

Product 1

HCID 44818987DG 051 (HCl salt)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product from step 5 (2.20 g, 5.45 mmol) in MeOH (22 mL) was added 2N NaOH (7.23 mL, 14.5 mmol). The resulting purplish-pink solution was stirred at ambient temperature overnight. The solvent was removed in vacuo. The crude oil was dissolved in water (45 mL) and the pH was adjusted to 7 with 2N HCl solution. The crude residue was extracted into ethyl acetate. The combined organic portions were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel flash chromatography using MeOH/dichloromethane (gradient system) to give the free base of the title compound as a yellow oil. To the subsequent oil was added 2M HCl in diethyl ether (35 mL). The resulting mixture was stirred at ambient temperature for 2 hours. The solvents were decanted. The remaining white solid was triturated in diethyl ether (50 mL) for 1 hour. The slurry was filtered, washed with diethyl ether (25 mL×3) and dried in vacuo at 45° C. for 48 hours to afford the title compound as a white solid (0.84 g, 36%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe crude oil was dissolved in water (45 mL)
  3. extractionThe crude residue was extracted into ethyl acetate
  4. washThe combined organic portions were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c74385c3c06a45b798028dcb2864d29a
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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