Hydrochloric Acid → HCID 54596157, compound

HRID 1186251Notes

Reaction equation

HRID 1186251 reaction equation
[C:1]([C:5]1[CH:42]=[CH:41][C:8]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:20]=2[CH2:19][CH:18]([N:21]([CH2:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37]C)=[O:36])=[CH:33][CH:32]=2)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]C)=[O:27])[CH2:17][CH2:16]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO.O1CCOCC1.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:20]=2[CH2:19][CH:18]([N:21]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:35]([OH:37])=[O:36])=[CH:39][CH:40]=2)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:17][CH2:16]3)=[CH:41][CH:42]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68213456HCID 68213456, compound

Product 1

HCID 54596157HCID 54596157, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

68.5 mg (0.12 mmol) of the compound from Example 5A were dissolved in 0.5 ml of methanol and 1 ml of dioxane, 0.15 ml of 45% strength aqueous sodium hydroxide solution and 0.2 ml of water were added and the mixture was then stirred at a bath temperature of 100° C. for 45 min. The milky suspension was then diluted with water, acidified with 2 N hydrochloric acid and extracted repeatedly with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC (method 1).

Workup

  1. extractionextracted repeatedly with dichloromethane
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC (method 1)

Sources & evidence

ORD record
ord-718f98f19e1e4dd7808a5724ba1af2ca
Source dataset
uspto-grants-2014_03
Patent number
US08673903B2

Reaction notes

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