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

HRID 987279Notes

Reaction equation

HRID 987279 reaction equation
C([O:3][C:4](=[O:30])[C@@H:5]([O:27][CH2:28][CH3:29])[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][CH3:26])=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)C.[OH-].[Li+].Cl>O1CCCC1.O>[CH2:28]([O:27][C@@H:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]([O:25][CH3:26])=[O:24])=[CH:20][CH:21]=2)=[CH:9][CH:8]=1)[C:4]([OH:30])=[O:3])[CH3:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 53794173(S)-2-ethoxy-3-(4-[2-{4-(methoxycarbonylamino)phenyl}ethoxy]phenyl)propanoic acid ethyl ester

Product 1

HCID 9843204(S)-2-ethoxy-3-[4-{2-[4-(methoxycarbonylamino)phenyl)ethoxy]phenyl}propanoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-Ethoxy-3-(4-[2-{4-(methoxycarbonylamino)phenyl]ethoxy]phenyl)propanoic acid ethyl ester (described in Example 41) (0.52 g; 1.25 mmole) was dissolved in tetrahydrofuran (10 ml) and lithium hydroxide (0.034 g; 1.42 mmole) dissolved in water (2 ml) was added slowly. The reaction mixture was stirred over night, hydrochloric acid (1 M, 1 ml) was added and tetrahydrofuran evaporated. The residue was extracted three times with ethyl acetate. The organic phase was dried with magnesium sulfate and evaporated and 0.47 g (99% yield) (S)-2-ethoxy-3-[4-{2-[4-(methoxycarbonylamino)phenyl)ethoxy]phenyl}propanoic acid was obtained.

Workup

  1. additionwas added slowly
  2. customtetrahydrofuran evaporated
  3. extractionThe 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-2417b3af949043038f87525c6bdf12cf
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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