Water → HCID 178418901, compound

HRID 7348Notes

Reaction equation

HRID 7348 reaction equation
[ClH:1].[NH2:2][CH:3]([C:26]([O:28][CH3:29])=[O:27])[CH2:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:23]=[CH:22][C:13]([CH:14]=[C:15]3[S:19][C:18](=[O:20])[NH:17][C:16]3=[O:21])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1.C1([N:36]=[C:37]=[N:38][CH:39]2[CH2:44][CH2:43][CH2:42]C[CH2:40]2)CCCCC1.[OH2:45].C[N:47](C)C=O>>[ClH:1].[ClH:1].[NH2:47][CH:43]([CH2:44][C:39]1[N:38]=[CH:37][NH:36][CH:40]=1)[C:42]([NH:2][CH:3]([C:26]([O:28][CH3:29])=[O:27])[CH2:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:23]=[CH:22][C:13]([CH2:14][CH:15]3[S:19][C:18](=[O:20])[NH:17][C:16]3=[O:21])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)=[O:45]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 730387885[4-(4-(2-Amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride

Product 1

HCID 178418901HCID 178418901, compoundYield 51%

Procedure

A solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride (6 g, 13.7 mmol) and 2-N-t-butoxy-carbonylamino-4-imidazole propionic acid (5.2 g, 20.3 mmol) in N,N-dimethylformamide (200 ml) was stirred for 1 h at −10° C. N,N′-Dicyclohexylcarbodiimide (4.5 g, 21.8 mmol) was added to this solution and stirring was continued for 12 h at ambient temperature. Water (1800 ml) was added to the reaction mixture, stirred for 20 minutes and extracted with ethyl acetate (3×400 ml). Ethyl acetate extract was washed with water (300 ml), dried over anhydrous sodium sulfate and concentrated to furnish the title compound, which was purified by column chromatography (3.4 g, yield 51%).

Workup

  1. stirringstirred for 20 minutes
  2. extractionextracted with ethyl acetate (3×400 ml)
  3. extractionEthyl acetate extract
  4. washwas washed with water (300 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-26ebee2f65de419a88e12f4b2597d1eb
Source dataset
uspto-grants-2006_08
Patent number
US07087576B2

Reaction notes

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