Glycine → HCID 136180192, compound

HRID 486100Notes

Reaction equation

HRID 486100 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].CC(C)([O-])C.[K+].[CH3:12][C:13]([C:16]1[CH:17]=[C:18]([CH:27]=[C:28]2[S:32][C:31](SC)=[N:30][C:29]2=[O:35])[CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[OH:22])([CH3:15])[CH3:14]>C(O)C>[CH3:15][C:13]([C:16]1[CH:17]=[C:18]([CH:27]=[C:28]2[S:32][C:31](=[N:1][CH2:2][C:3]([OH:5])=[O:4])[NH:30][C:29]2=[O:35])[CH:19]=[C:20]([C:23]([CH3:24])([CH3:25])[CH3:26])[C:21]=1[OH:22])([CH3:12])[CH3:14]

Participants

5

Reactant 3

HCID 750GlycineHCID 23665647Potassium tert-butoxideHCID 53858627HCID 53858627, compound

Product 1

HCID 136180192HCID 136180192, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of glycine (2.25 g, 0.03 mole), potassium-t-butoxide (2.81 g, 0.025 mole), and ethanol (700 mL) is stirred at room temperature for 15 minutes. 5-[(3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl)methylene]-2-(methylthio)-4(5H)-thiazolone (7.27 g, 0.02 mole) is added to it and the mixture is refluxed with stirring for 20 hours. The mixture is then filtered and the solvent removed at 40° C. under reduced pressure. The residue is treated with ice-water, acidified with 1N aqueous hydrochloric acid and extracted with ether. The organic layer is washed with water, dried, and the solvent removed to give 7.75 g of a solid. The crude solid is recrystallized from tetrahydrofuran-ether to give 2.95 g (38%) of pure N-[5-[3,5-[bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4-oxo-2-thiazolidinylidene]glycine, (Z)-, mp 260° C. (dec). Anal. for C20H26N2O4S.0.25C4H8O: Calcd: C, 61.74; H, 6.91; N, 6.86; S, 7.85. Found: C, 61.82; H, 7.08; N, 6.50; S, 7.55.

Workup

  1. temperaturethe mixture is refluxed
  2. stirringwith stirring for 20 hours
  3. filtrationThe mixture is then filtered
  4. customthe solvent removed at 40° C. under reduced pressure
  5. additionThe residue is treated with ice-water
  6. extractionextracted with ether
  7. washThe organic layer is washed with water
  8. customdried
  9. customthe solvent removed

Sources & evidence

ORD record
ord-4d7058d3d3b94a20b8840c8bddb7a459
Source dataset
uspto-grants-1994_03
Patent number
US05290800

Reaction notes

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