Lithium Hydroxide → HCID 66962521, compound

HRID 1362895Notes

Reaction equation

HRID 1362895 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C@H:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C@@H:11]1[C:23]([O:25]C)=[O:24].[OH-].[Li+]>O1CCCC1.CO>[C:19]([O:18][C:16]([N:13]1[CH2:14][CH2:15][C@H:10]([C:3]2[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=2[F:1])[C@@H:11]([C:23]([OH:25])=[O:24])[CH2:12]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86619289HCID 86619289, compound

Product 1

HCID 66962521HCID 66962521, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 3.3 g (15 mmol) of the product of Step B in 200 mL of 3:1 tetrahydrofuran/methanol was added 50 mL (50 mmol) of 1N aqueous lithium hydroxide solution and the resulting solution was stirred at ambient temperature for 16 h, then concentrated and acidified with 100 mL of 1N aqueous hydrochloric acid. The resulting mixture was extracted with three 100-mL portions of ethyl acetate, and the organic phases combined and washed sequentially with 1N hydrochloric acid and saturated aqueous brine (100 mL each). The organic phase was dried over magnesium sulfate, filtered, and evaporated in vacuo to yield the title compound as a colorless foamy solid that was used without further purification. LC/MS 382.4 (M+23).

Workup

  1. concentrationconcentrated
  2. extractionThe resulting mixture was extracted with three 100-mL portions of ethyl acetate
  3. washwashed sequentially with 1N hydrochloric acid and saturated aqueous brine (100 mL each)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-65513e0b144741bf9ee3a688ea1bb650
Source dataset
uspto-grants-2011_02
Patent number
US07884104B2

Reaction notes

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