Beta-Alanine → HCID 21816497, compound

HRID 543864Notes

Reaction equation

HRID 543864 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[K+].[C:9](=[S:11])=[S:10].[CH2:12](Br)[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]>O.CO>[C:15]1([C:13]2([OH:14])[CH2:12][S:10][C:9](=[S:11])[N:1]2[CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 239Beta-AlanineHCID 6259Phenacyl bromideHCID 6348Carbon DisulfideHCID 14797Potassium Hydroxide

Product 1

HCID 21816497HCID 21816497, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To 250 ml of a methanol solution containing 44 g (0.5 mol) of β-aminopropionic acid and 28 g (0.5 mol) of potassium hydroxide, was added 30 ml (0.5 mol) of carbon disulfide under cooling (at 5° C. or below) and the mixture was stirred for 2 hours. A methanol solution containing 100 g (0.5 mol) of phenacyl bromide was added dropwise under cooling at 5° C. or below and after the completion of the addition the mixture was stirred at room temperature for 2.5 hours. 220 ml of water was added and the alcohol was distilled off under reduced pressure. The residue was acidified with hydrochloric acid (at pH of about 3 or 4) under cooling with ice with stirring and the crystals thus-deposited were collected and washed with water to obtain 116 g of 4-phenyl-3-(2-carboxyethyl)-4-hydroxythiazolidine-2-thione. Melting point of the compound was 132° C. The crystals were dissolved in 500 ml of glacial acetic acid and refluxed by heating for 30 minutes. After cooling, 1 liter of water was added to the mixture and the crystals thus-deposited were collected by filtration to obtain 89 g (yield 65%) of the desired compound. Melting point of the compound was 134° to 136° C.

Workup

  1. temperatureunder cooling (at 5° C. or below)
  2. additionwas added dropwise
  3. temperatureunder cooling at 5° C. or below
  4. additionafter the completion of the addition the mixture
  5. stirringwas stirred at room temperature for 2.5 hours
  6. distillationthe alcohol was distilled off under reduced pressure
  7. temperatureunder cooling with ice
  8. stirringwith stirring
  9. customthe crystals thus-deposited were collected
  10. washwashed with water

Sources & evidence

ORD record
ord-8c04f84ec0d34a618c6b15208a4cc9a3
Source dataset
uspto-grants-1984_05
Patent number
US04447522

Reaction notes

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