Hydrochloric Acid → 3-[4-{2-(4-[benzyloxycarbonylamino]-phenyl)ethoxy}phenyl]-(S)-2-ethoxypropanoic acid

HRID 987291Notes

Reaction equation

HRID 987291 reaction equation
C([O:3][C:4](=[O:36])[C@@H:5]([O:33][CH2:34][CH3:35])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)C.[OH-].[Li+].Cl>O1CCCC1.O>[CH2:26]([O:25][C:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][O:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:33][CH2:34][CH3:35])[C:4]([OH:36])=[O:3])=[CH:12][CH:11]=2)=[CH:17][CH:18]=1)=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 542299253-[4-{2-(4-[benzyloxycarbonylamino]phenyl)ethoxy}phenyl]-(S)-2-ethoxypropanoic acid ethyl ester

Product 1

HCID 99122343-[4-{2-(4-[benzyloxycarbonylamino]-phenyl)ethoxy}phenyl]-(S)-2-ethoxypropanoic acidYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[4-{2-(4-[Benzyloxycarbonylamino]phenyl)ethoxy}phenyl]-(S)-2-ethoxypropanoic acid ethyl ester (described in Example 52) (0.16 g; 0.32 mmole) was dissolved in tetrahydrofuran and lithium hydroxide (9 mg; 0.38 mmole) dissolved in water (1 ml) was added. The resulting mixture was stirred over night. Hydrochloric acid (1M; 1 ml) was added. Tetrahydrofuran was evaporated and the remaining water residue was extracted three times with ethyl acetate. The organic phase was dried with magnesium sulfate and evaporated to give 0.14 g (92.8% yield) of 3-[4-{2-(4-[benzyloxycarbonylamino]-phenyl)ethoxy}phenyl]-(S)-2-ethoxypropanoic acid.

Workup

  1. additionwas added
  2. customTetrahydrofuran was evaporated
  3. extractionthe remaining water residue was extracted three times with ethyl acetate
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-8d887dcf1a484f99b28ac3843e2c2a45
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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