Water → HCID 178418901, compound

HRID 2111875Notes

Reaction equation

HRID 2111875 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]([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.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 219896812-Amino-3-[4-[4-[(2,4-dioxo-5-thiazolidinyl)methyl]phenoxy]phenyl]propanoic acid methyl ester hydrochloride

Product 1

HCID 178418901HCID 178418901, compoundYield 86%

Procedure

A solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione hydrochloride (4 g, 9.16 mmol) and 2-N-t-butoxycarbonylamino-4-imidazole propionic acid (3.2 g, 12.82 mmol) in N,N-dimethylformamide (50 ml) was stirred for 1 h at −10° C. N,N′-Dicyclohexylcarbodiimide (3.01 g, 14.65 mmol) was added to this solution and stirred for 10 h at ambient temperature. Water (600 ml) was added to the reaction mixture, stirred for 20 minutes and extracted with ethyl acetate (3×300 ml). Ethyl acetate extract was washed with water (100 ml), dried over anhydrous sodium sulfate and concentrated to give the title compound, (5 g, yield 86%).

Workup

  1. stirringstirred for 20 minutes
  2. extractionextracted with ethyl acetate (3×300 ml)
  3. extractionEthyl acetate extract
  4. washwas washed with water (100 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2fbc53fe128e4248a63ce2addb69f57e
Source dataset
uspto-grants-2009_04
Patent number
US07521466B2

Reaction notes

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