Lithium Hydroxide → HCID 53379068, compound

HRID 714736Notes

Reaction equation

HRID 714736 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[C:10]([CH2:18][N:19]2[C:23](=[O:24])[N:22]([CH2:25][CH:26]([OH:31])[C:27]([F:30])([F:29])[F:28])[C:21]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)=[N:20]2)[CH:9]=1.[OH-].[Li+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[C:10]([CH2:18][N:19]2[C:23](=[O:24])[N:22]([CH2:25][CH:26]([OH:31])[C:27]([F:28])([F:29])[F:30])[C:21]([C:32]3[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=3)=[N:20]2)[CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69940682HCID 69940682, compound

Product 1

HCID 53379068HCID 53379068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

204 mg (0.36 mmol) of the compound from Example 129 were dissolved in 3 ml of THF, and 0.4 ml of a 1 N aqueous lithium hydroxide solution was added. The mixture was stirred at RT for 20 h. For work-up, the solvent was removed under reduced pressure, the residue was taken up in about 5 ml of water and 0.07 ml of 6 N hydrochloric acid was added. The precipitated solid was filtered off with suction and dried. Further purification of the crude product was carried out by chromatography on silica gel (mobile phase: first cyclohexane/ethyl acetate 1:3, then pure ethyl acetate, finally dichloromethane/methanol 1:1). This gave 97 mg (47% of theory) of the target compound.

Workup

  1. customFor work-up, the solvent was removed under reduced pressure
  2. addition0.07 ml of 6 N hydrochloric acid was added
  3. filtrationThe precipitated solid was filtered off with suction
  4. customdried
  5. customFurther purification of the crude product

Sources & evidence

ORD record
ord-797c511e935941a88ea8cffeb4600a54
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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