Lithium Hydroxide → 3-[4-(2-{4-Tert-butoxycarbonylaminophenyl}ethoxy)phenyl]-2-(2,2,2-trifluoroethoxy)propanoic acid

HRID 987304Notes

Reaction equation

HRID 987304 reaction equation
C[O:2][C:3](=[O:35])[CH:4]([O:29][CH2:30][C:31]([F:34])([F:33])[F:32])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1.[OH-].[Li+]>O1CCCC1.O>[C:25]([O:24][C:22]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([O:29][CH2:30][C:31]([F:32])([F:33])[F:34])[C:3]([OH:35])=[O:2])=[CH:7][CH:8]=2)=[CH:20][CH:19]=1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 571530703-[4-(2-{4-tert-Butoxycarbonylaminophenyl}ethoxy)phenyl]-2-(2,2,2-trifluoroethoxy)propanoic acid methyl ester

Product 1

HCID 229886913-[4-(2-{4-Tert-butoxycarbonylaminophenyl}ethoxy)phenyl]-2-(2,2,2-trifluoroethoxy)propanoic acidYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3-[4-(2-{4-tert-Butoxycarbonylaminophenyl}ethoxy)phenyl]-2-(2,2,2-tnifluoroethoxy)propanoic acid methyl ester (described in Example 60)(0.27 g; 0.52 mmole) was dissolved in tetrahydrofuran and water (2:1), lithium hydroxide (0.015 g; 0.62 mmole) was added and the reaction mixture was stirred over night. Water was added and tetrahydrofuran was evaporated. The remaining water residue was extracted once with diethyl ether, acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate. Evaporation gave 0.22 g (85% yield) of 3-[4-(2-{4-tert-butoxycarbonylaminophenyl}ethoxy)phenyl]-2-(2,2,2-trifluoroethoxy)propanoic acid.

Workup

  1. customtetrahydrofuran was evaporated
  2. extractionThe remaining water residue was extracted once with diethyl ether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. customEvaporation

Sources & evidence

ORD record
ord-7650a6ea5b364ebdace6252389d7cdc5
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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