Water → 3-[4-(Benzyloxy)phenyl]-2-ethoxypropanoic acid

HRID 411877Notes

Reaction equation

HRID 411877 reaction equation
C1(NCCO)C=CC=CC=1.[CH2:11]([O:13][C@@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)[C:15]([OH:17])=[O:16])[CH3:12].O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH2:11]([O:13][CH:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)[C:15]([OH:17])=[O:16])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 70017024(S)-2-ethoxy-3-(4-benzyloxyphenyl) propanoic acid phenyl glycinol salt

Product 1

HCID 109245703-[4-(Benzyloxy)phenyl]-2-ethoxypropanoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
12.5 °C

Procedure

A mixture of (S)-2-ethoxy-3-(4-benzyloxyphenyl)propanoic acid α-methyl benzyl amino salt of the formula (12) or (S)-2-ethoxy-3-(4-benzyloxyphenyl) propanoic acid phenyl glycinol salt of the formula (18), (6.7 g) water (70 ml) and toluene (35 ml) was taken in a reaction flask and stirred for 5-10 min. The reaction mass was cooled to 10-15° C. and 25% cold sulfuric acid was added slowly to adjust pH of the reaction mass to 2. Aqueous and organic layers were separated. Aqueous layer was extracted with toluene (35 ml). The combined toluene layers were washed with water (20 ml) and evaporated to yield (S) 2-ethoxy-3-(4-benzyloxyphenyl)propanoic acid the formula (9b) (4 g).

Workup

  1. customwas taken in a reaction flask
  2. customAqueous and organic layers were separated
  3. extractionAqueous layer was extracted with toluene (35 ml)
  4. washThe combined toluene layers were washed with water (20 ml)
  5. customevaporated

Sources & evidence

ORD record
ord-d78cfc5a2c9c481fa7014e48cbd7d875
Source dataset
uspto-grants-2003_05
Patent number
US06559335B2

Reaction notes

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