Lithium Hydroxide → (2S)-3-[4-(3-{4-[(tert-Butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoic acid

HRID 1375722Notes

Reaction equation

HRID 1375722 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C@H:26]([O:32][CH2:33][CH3:34])[C:27]([O:29]CC)=[O:28])=[CH:21][CH:20]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C@H:26]([O:32][CH2:33][CH3:34])[C:27]([OH:29])=[O:28])=[CH:23][CH:24]=2)=[CH:13][CH:14]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 86613339Ethyl (2S)-3-[4-(3-{4-[(tert-butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoate

Product 1

HCID 69424279(2S)-3-[4-(3-{4-[(tert-Butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoic acidYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (2S)-3-[4-(3-{4-[(tert-butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoate (350 mg, 0.742 mmol) was dissolved in THF (10 ml). Under stirring, lithium hydroxide in water (5 ml) was added. The mixture was stirred at room temperature and followed by HPLC. After 4 hours, the reaction was stopped. More lithium hydroxide (9 mg) was added. The mixture was stirred overnight. It was then evaporated in vacuum to remove THF. The residue was extracted with diethyl ether and then acidified with 10% hydrochloric acid, pH˜3, and extracted with ethyl acetate (×2). The organic phases were combined and washed with brine and dried with magnesium sulfate. The solvent was evaporated and white solid product (315 mg) was left, yield 96%.

Workup

  1. stirringThe mixture was stirred at room temperature
  2. stirringThe mixture was stirred overnight
  3. customIt was then evaporated in vacuum
  4. customto remove THF
  5. extractionThe residue was extracted with diethyl ether
  6. extractionextracted with ethyl acetate (×2)
  7. washwashed with brine
  8. dry with materialdried with magnesium sulfate
  9. customThe solvent was evaporated
  10. waitwhite solid product (315 mg) was left

Sources & evidence

ORD record
ord-8d393408841d4045afec8df5c8ded59f
Source dataset
uspto-grants-2007_01
Patent number
US07169810B2

Reaction notes

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