Ethacrynic Acid → N-[3-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetylthio-2-methylpropanoyl]-N-cyclopentyl glycine t-butyl ester

HRID 543263Notes

Reaction equation

HRID 543263 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]([C:14](=[O:19])[CH:15]([CH3:18])[CH2:16][SH:17])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][CH2:22][C:23]([C:25]([C:27]1[CH:28]=[CH:29][C:30]([O:35][CH2:36][C:37](O)=[O:38])=[C:31]([Cl:34])[C:32]=1[Cl:33])=[O:26])=[CH2:24]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]([C:14](=[O:19])[CH:15]([CH3:18])[CH2:16][S:17][C:37](=[O:38])[CH2:36][O:35][C:30]1[CH:29]=[CH:28][C:27]([C:25](=[O:26])[C:23](=[CH2:24])[CH2:22][CH3:21])=[C:32]([Cl:33])[C:31]=1[Cl:34])[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 3278Ethacrynic AcidHCID 13469597N-(3-mercapto-2-methylpropanoyl)-N-cyclopentylglycine t-butyl ester

Product 1

HCID 20205973N-[3-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetylthio-2-methylpropanoyl]-N-cyclopentyl glycine t-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution containing 19.2 g (63.8 mmol) of N-(3-mercapto-2-methylpropanoyl)-N-cyclopentylglycine t-butyl ester and 19.3 g (63.7 mmol) of ethacrynic acid in 20 ml of methylene chloride at 0° C. was added a solution of 13.2 g (64.0 mmol) of N,N-dicyclohexylcarbodiimide in 20 ml of methylene chloride. The solution was allowed to warm to room temperature and to stir overnight. The solution was filtered and the filtrate was concentrated in vacuo. Purification of the product by HPLC [10% ethyl acetate in hexanes] afforded N-[3-[2,3-dichloro-4-(2-methylene-1-oxobutyl) phenoxy] acetylthio-2-methylpropanoyl]-N-cyclopentyl glycine t-butyl ester as a viscous oil.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification of the product by HPLC [10% ethyl acetate in hexanes]

Sources & evidence

ORD record
ord-1a621152847745cbb534581cd1f49eb9
Source dataset
uspto-grants-1987_04
Patent number
US04661515

Reaction notes

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