L-Aspartic Acid → HCID 131719727, compound

HRID 1901421Notes

Reaction equation

HRID 1901421 reaction equation
C1S(=O)(=O)CCC1.[NH2:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][C:12]([OH:14])=[O:13].[NH2:18][C@H:19]([C:24]([OH:26])=[O:25])[CH2:20][C:21]([OH:23])=[O:22].[NH2:27][C@H:28]([C:37]([OH:39])=[O:38])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1.[NH2:40][C@H:41]([C:49]([OH:51])=[O:50])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O>[NH2:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][C:12](=[O:13])[OH:14].[NH2:18][C@H:19]([C:24]([OH:26])=[O:25])[CH2:20][C:21](=[O:22])[OH:23].[NH2:27][C@H:28]([C:37]([OH:39])=[O:38])[CH2:29][C:30]1[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=1.[NH2:40][C@H:41]([C:49]([OH:51])=[O:50])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

7

Reactant 5

HCID 5960L-Aspartic AcidHCID 6057L-TyrosineHCID 6140L-PhenylalanineHCID 31347SulfolaneHCID 33032L-Glutamic Acid

Product 1

HCID 131719727HCID 131719727, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

750 ml of tetramethylene sulfone was heated to 190° C. in an inert nitrogen atmosphere in a 4 liter flask with stirring. 294 g of glutamic acid was added and the mixture was heated for one-half hour. 266 g of aspartic acid was added and the mixture heated as rapidly as possible to 190° C. and held there for 15 minutes. 362 g of tyrosine was added and the mixture heated at 190° C. for 3 hours. 330 g of phenylalanine was added and the mixture heated at 190° C. for 1.5 hours. The hot melt was then poured into 5 liters of water with vigorous stirring. After stirring for about 1 hour, the mixture was filtered and the filtrate discarded. The cake was reslurried in 5 liters of water, filtered and the cake was again reslurried in 5 liters of water. The pH of the slurry (at 25° C.) was adjusted to 8 using 40% sodium hydroxide solution. The mixture was filtered and the cake washed with a small amount of water. The washes and filtrate are combined and evaporated to dryness in vacuo to give Glu/Asp/Tyr/Phe proteinoid.

Workup

  1. temperaturethe mixture was heated for one-half hour
  2. temperaturethe mixture heated at 190° C. for 3 hours
  3. temperaturethe mixture heated at 190° C. for 1.5 hours
  4. stirringAfter stirring for about 1 hour
  5. filtrationthe mixture was filtered
  6. filtrationfiltered
  7. customThe pH of the slurry (at 25° C.)
  8. filtrationThe mixture was filtered
  9. washthe cake washed with a small amount of water
  10. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-bf6d88ef78834b8e9591108c5275fa46
Source dataset
uspto-grants-1996_11
Patent number
US05578323

Reaction notes

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