Lithium hydroxide, monohydrate → HCID 22988688, compound

HRID 987284Notes

Reaction equation

HRID 987284 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([O:30][CH2:31][CH3:32])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:18][CH:17]=2)[CH:8]=1)C.O.[OH-].[Li+]>O1CCCC1.O>[C:26]([O:25][C:23]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][O:13][C:9]2[CH:8]=[C:7]([CH2:6][CH:5]([O:30][CH2:31][CH3:32])[C:4]([OH:33])=[O:3])[CH:12]=[CH:11][CH:10]=2)=[CH:21][CH:20]=1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 53896856HCID 53896856, compound

Product 1

HCID 22988688HCID 22988688, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-{3-[2-(4-tert-Butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester (described in Example 48) (0.8 g; 1.74 mmole) was dissolved in tetrahydrofuran (15 ml). Lithium hydroxide hydrate (0.073 g; 1.74 mmole) dissolved in water (5 ml) was added slowly. The reaction mixture was stirred at room temperature for 4.5 hours. More lithium hydroxide hydrate (0.036 g; 0.87 mmole) was added and the stirring continued for 2 more hours. Tetrahydrofuran was carefully evaporated and a large amount of water was added. pH was adjusted to about 12 with sodium hydroxide (2M) and the solution was extracted with ethyl acetate. The water phase was cooled to <10° C., acidified with potassium hydrogensulfate (1 M) and extracted with ethyl acetate. The organic phase was washed with water and dried with sodium sulfate. Evaporation gave 0.53 g (70.9% yield) of 3-{3-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid.

Workup

  1. additionwas added slowly
  2. customTetrahydrofuran was carefully evaporated
  3. additiona large amount of water was added
  4. extractionthe solution was extracted with ethyl acetate
  5. temperatureThe water phase was cooled to <10° C.
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with water
  8. dry with materialdried with sodium sulfate
  9. customEvaporation

Sources & evidence

ORD record
ord-05f146bc19fe4132983e67a71cb4f0ab
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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