Lithium Hydroxide → HCID 67076738, compound

HRID 521449Notes

Reaction equation

HRID 521449 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)[CH:5]=1.[OH-].[Li+]>O1CCOCC1>[C:21]([C:17]1[CH:16]=[C:15]([CH2:14][CH2:13][O:12][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=2[O:10][CH3:11])[C:3]([OH:23])=[O:2])[CH:20]=[CH:19][CH:18]=1)#[N:22]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67076577HCID 67076577, compound

Product 1

HCID 67076738HCID 67076738, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

The compound of step 2 (274 mg, 0.883 mmol) was dissolved in dioxane (4.5 ml), lithium hydroxide (4.42 ml of a 1 M aqueous solution, 4.42 mmol) was added, and the mixture was stirred at 60° C. for 30 min. The mixture was partitioned between 2 N hydrochloric acid and EA, the aqueous phase extracted with EA, and the combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by preparative RP HPLC (water/ACN gradient) to give 160 mg of the title compound.

Workup

  1. customThe mixture was partitioned between 2 N hydrochloric acid and EA
  2. extractionthe aqueous phase extracted with EA
  3. dry with materialthe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-cf86cd25eae94e48befd17466a91adfc
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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