Acetic Anhydride → 5-[1-(2-Acetylaminothiazol-4-yl)-1-ethoxycarbonylmethylene]-2,4-dioxothiazolidine-3-acetic acid

HRID 2107174Notes

Reaction equation

HRID 2107174 reaction equation
[CH2:1]([O:3][C:4]([C:6]([CH:23]1[S:27][C:26](=[O:28])[N:25]([CH2:29][C:30]([OH:32])=[O:31])[C:24]1=[O:33])(O)[C:7]1[N:8]=[C:9]([NH:12][C:13](NC2C=CC=CC=2)=[O:14])[S:10][CH:11]=1)=[O:5])[CH3:2].[C:34]1(NC(=O)NC2SC=C(C(=O)C(OCC)=O)N=2)C=CC=CC=1.O=C1N(CC(O)=O)C(=O)CS1.N1CCCCC1.C(OC(=O)C)(=O)C>O.N1C=CC=CC=1.C(O)C>[C:13]([NH:12][C:9]1[S:10][CH:11]=[C:7]([C:6](=[C:23]2[S:27][C:26](=[O:28])[N:25]([CH2:29][C:30]([OH:32])=[O:31])[C:24]2=[O:33])[C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:8]=1)(=[O:14])[CH3:34]

Participants

9

Reactant 5

HCID 7918Acetic AnhydrideHCID 8082PiperidineHCID 2770836(2,4-Dioxo-1,3-thiazolidin-3-yl)acetic acidHCID 15053489Ethyl 2-(3-phenylureido)thiazol-4-ylglyoxylateHCID 230475735-{1-Ethoxycarbonyl-1-hydroxy-1-[2-(3-phenylureido)thiazol-4-yl]methyl}-2,4-dioxothiazolidine-3-acetic acid

Product 1

HCID 539168005-[1-(2-Acetylaminothiazol-4-yl)-1-ethoxycarbonylmethylene]-2,4-dioxothiazolidine-3-acetic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture comprising 0.6 g of crude 5-{1-ethoxycarbonyl-1-hydroxy-1-[2-(3-phenylureido)thiazol-4-yl]methyl}-2,4-dioxothiazolidine-3-acetic acid [prepared from 2.6 g of ethyl 2-(3-phenylureido)thiazol-4-ylglyoxylate, 1.2 g of 2,4-dioxothiazolidine-3-acetic acid, 1.2 g of piperidine and 30 ml of ethanol by a procedure similar to that of Example 24], 0.5 g of acetic anhydride and 4 ml of pyridine was heated at 60° C. for 17 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure. The resulting oil was purified by silica gel column chromatography, using as eluent a 8:2:0.5 to 7:3:0.5 by volume mixture of benzene ethyl acetate and acetic acid, giving the desired compound as a yellow powder having the following physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated off under reduced pressure
  4. customThe resulting oil was purified by silica gel column chromatography
  5. additionby volume mixture of benzene ethyl acetate and acetic acid

Sources & evidence

ORD record
ord-77291116254c4c11b1dc110fd7121297
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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