Lithium Hydroxide → HCID 69371571, compound

HRID 1372469Notes

Reaction equation

HRID 1372469 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)/[CH:15]=[CH:16]/[CH3:17])[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:14]([C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:22][CH:23]=1)/[CH:15]=[CH:16]/[CH3:17])[C:10]([OH:12])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69417670HCID 69417670, compound

Product 1

HCID 69371571HCID 69371571, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of the product from Step E (3.55 g, 8.9 mmol) in 250 mL of 3:1:1 tetrahydrofuran/methanol/1N aqueous lithium hydroxide solution (50 mL, 50 mmol) was stirred at room temperature for 15 h then concentrated and acidified with 200 mL of 10% aqueous hydrochloric acid. The resultant mixture was then extracted with three 150-mL portions of ethyl acetate, the organic phases combined and washed sequentially with 5% 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 acid as a colorless foamy solid that was used without further purification. LC/MS 385.2 (M+1).

Workup

  1. concentrationthen concentrated
  2. extractionThe resultant mixture was then extracted with three 150-mL portions of ethyl acetate
  3. washwashed sequentially with 5% 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-111f0855a09e4839b945fdf14e02718c
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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