Water → 2-(2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}-1-methoxycarbonylethylcarbamoyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

HRID 7350

Reaction equation

HRID 7350 reaction equation
Cl.[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.[C:30]([O:34][C:35]([N:37]1[CH2:41][CH2:40][CH2:39][CH:38]1[C:42](O)=[O:43])=[O:36])([CH3:33])([CH3:32])[CH3:31].C1(N=C=NC2CCCCC2)CCCCC1.O>CN(C)C=O.C(OCC)(=O)C>[C:30]([O:34][C:35]([N:37]1[CH2:41][CH2:40][CH2:39][CH:38]1[C:42](=[O:43])[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:36])([CH3:33])([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 2684721-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 219896812-Amino-3-[4-[4-[(2,4-dioxo-5-thiazolidinyl)methyl]phenoxy]phenyl]propanoic acid methyl ester hydrochloride

Product 1

HCID 865974422-(2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}-1-methoxycarbonylethylcarbamoyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl EsterYield 51.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione hydrochloride (2.03 g, 4.65 mmol) and N-t-butoxycarbonylpyrrolidin-2-carboxylic acid (1 g, 4.65 mmol) in N,N-dimethylformamide (20 ml) was stirred for 1 h at 0° C. N,N′-Dicyclohexylcarbodiimide (0.96 g, 4.65 mmol) was added to this solution and stirring was continued for 2 h at ambient temperature. Water (150 ml) was added to the reaction mixture, stirred for 20 minutes, ethyl acetate (200 ml) was added and stirring continued for another 15 minutes. The organic layer was separated and washed with water (100 ml), dried over anhydrous sodium sulfate and concentrated to give the crude compound, which was purified by column chromatography (1.42 g, yield 51.2%).

Workup

  1. stirringstirred for 20 minutes
  2. stirringstirring
  3. waitcontinued for another 15 minutes
  4. customThe organic layer was separated
  5. washwashed with water (100 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-964f5c140dda483dbe6b8a944fee6afc
Source dataset
uspto-grants-2006_08
Patent number
US07087576B2

Linked notes

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