Beta-Alanine → HCID 9969989, compound

HRID 609881Notes

Reaction equation

HRID 609881 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[NH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22].[SH:24][CH2:25][C:26](O)=[O:27]>C1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]2[N:18]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:26](=[O:27])[CH2:25][S:24]2)[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 1133Thioglycolic AcidHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 9969989HCID 9969989, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In benzene (500 ml) were suspended 3,5-di-tert-butyl-4-hydroxybenzaldehyde (50.0 g) and β-alanine (20.0 g) under a nitrogen atmosphere. A Dean-Stark trap was fitted to the reactor, and the suspension was refluxed for 1 hour. After allowing the mixture to cool, α-mercaptoacetic acid (23.6 g) was added, then the mixture was further refluxed for 24 hours. After removal of benzene by evaporation, water (500 ml) was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 98:2) to afford 54.6 g (67%) of 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-(2-carboxyethyl)-1,3-thiazolidin-4-one as colorless crystals. mp 164-165° C. NMR (CDCl3, 200 MHz) δ: 1.42 (18H, s), 2.2-2.5 (1H, m), 2.5-2.8 (1H, m), 3.0-3.3 (1H, m), 3.5-4.0 (3H, m), 5.33 (1H, s), 5.64 (1H, s), 7.09 (2H, s), 8.5 (1H, brs)

Workup

  1. customA Dean-Stark trap was fitted to the reactor
  2. temperaturethe suspension was refluxed for 1 hour
  3. temperatureto cool
  4. temperaturethe mixture was further refluxed for 24 hours
  5. customAfter removal of benzene
  6. customby evaporation, water (500 ml)
  7. additionwas added to the residue
  8. extractionthe mixture was extracted with chloroform
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 98:2)

Sources & evidence

ORD record
ord-ad04ec329216432da343a52743dfdc33
Source dataset
uspto-grants-1999_12
Patent number
US05998452

Reaction notes

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