Lithium hydroxide, monohydrate → 3-{4-[2-(4-tert-Butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid

HRID 1375714Notes

Reaction equation

HRID 1375714 reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:36])[CH:8]([O:33][CH2:34][CH3:35])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)C>O.O1CCCC1>[C:29]([O:28][C:26]([NH:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][CH2:17][O:16][C:13]2[CH:12]=[CH:11][C:10]([CH2:9][CH:8]([O:33][CH2:34][CH3:35])[C:7]([OH:36])=[O:6])=[CH:15][CH:14]=2)=[CH:24][CH:23]=1)=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22988408Ethyl 3-(4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoate

Product 1

HCID 229884463-{4-[2-(4-tert-Butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acidYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide hydrate (77 mg; 1.85 mmole) in water (5.5 ml) was slowly added to a solution of 3-{4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester (0.77 g; 1.68 mmole) in tetrahydrofuran (7.6 ml). After stirring at room temperature for 4 hours the reaction mixture was kept in a freezer for 4 days. Tetrahydrofuran was removed by evaporation in vacuo. More water was added and the mixture was acidified with hydrochloric acid to pH 1. The product was extracted with ethyl acetate, washed twice with water, dried (sodium sulfate), filtered and the solvent was evaporated in vacuo to give 0.716 g of 3-{4-[2-(4-tert-butoxycarbonylaminophenyl)-ethoxy]phenyl}-2-ethoxypropanoic acid.

Workup

  1. waitwas kept in a freezer for 4 days
  2. customTetrahydrofuran was removed by evaporation in vacuo
  3. additionMore water was added
  4. extractionThe product was extracted with ethyl acetate
  5. washwashed twice with water
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-a52c49261e4f4ce9b99e025544c98c96
Source dataset
uspto-grants-2007_01
Patent number
US07169810B2

Reaction notes

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