Ethyl Acetate → 2-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acid

HRID 413786Notes

Reaction equation

HRID 413786 reaction equation
C([O:5][C:6](=[O:42])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]2[S:20][C:19](=[O:21])[N:18](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:17]2=[O:41])=[CH:11][CH:10]=1)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[O:21]=[C:19]1[NH:18][C:17](=[O:41])[CH:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:42])=[O:5])=[CH:10][CH:11]=2)[S:20]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 121120364-(2,4-Dioxo-3-tritylthiazolidin-5-ylmethyl)phenoxyacetic acid t-butyl ester

Product 1

HCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acidYield 83.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-(2,4-dioxo-3-tritylthiazolidin-5-ylmethyl)phenoxyacetic acid t-butyl ester (6.2 g) (obtained in Reference Example 5) in toluene (25 ml) was added p-toluenesulfonic acid monohydrate (204 mg). The resulting mixture was heated under reflux for 3 hours. Ethyl acetate (10 ml) was added while heating and then the mixture stirred at 25° C. for 1.5 hours. The resulting crystals were collected by filtration to afford the desired compound (2.5 g).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperaturewhile heating
  4. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-b59c13c995364b11ae90ad5d26b015e6
Source dataset
uspto-grants-2003_05
Patent number
US06569877B2

Reaction notes

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