Lithium Hydroxide → HCID 21107163, compound

HRID 1870048Notes

Reaction equation

HRID 1870048 reaction equation
C([O:3][C:4](=[O:32])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15]2[CH:16]=[C:17]3[C:22](=[C:23]([C:25]#[CH:26])[CH:24]=2)[O:21][C:20]([CH3:28])([CH3:27])[CH2:19][C:18]3([CH3:30])[CH3:29])=[O:13])=[CH:7][C:6]=1[F:31])C.[OH-].[Li+]>CO.O1CCCC1.O>[C:25]([C:23]1[CH:24]=[C:15]([NH:14][C:12](=[O:13])[NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:32])=[O:3])=[C:6]([F:31])[CH:7]=2)[CH:16]=[C:17]2[C:22]=1[O:21][C:20]([CH3:27])([CH3:28])[CH2:19][C:18]2([CH3:30])[CH3:29])#[CH:26]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 57424275HCID 57424275, compound2×

Product 1

HCID 21107163HCID 21107163, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[3-(8-ethynyl-2,2,4,4-tetramethyl-chroman-6-yl)-ureido]-2-fluoro-benzoic acid ethyl ester (Intermediate 212, 0.12 g) in methanol (2 mL), tetrahydrofuran (2 mL) and water (1 mL) was treated with lithium hydroxide (0.177 g, 4.2 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The volatiles were evaporated in vacuo, the residue was diluted with water and neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to afford the title compound as a solid (0.07 g, 46% for two steps).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with water and neutralized with dilute hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-dcc40386af28424e8a86d0635c76ae3a
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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