Dl-Phenylalanine → HCID 131713065, compound

HRID 435467Notes

Reaction equation

HRID 435467 reaction equation
[C:1]1([S:9]([OH:12])(=[O:11])=[O:10])([CH3:8])[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH2:2]1.[NH2:13][C@H:14]([C:22]([OH:24])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.NC(C(O)=O)CC1C=CC=CC=1.C(=O)C1C(=CC=CC=1)O.O.O.C1(S(O)(=O)=O)(C)C=CC(C)=CC1>CC(C)=O.C(O)=O>[C:1]1([S:9]([OH:12])(=[O:10])=[O:11])([CH3:8])[CH:2]=[CH:3][C:4]([CH3:7])=[CH:5][CH2:6]1.[NH2:13][CH:14]([C:22]([OH:24])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 994Dl-PhenylalanineHCID 6998SalicylaldehydeHCID 131713066HCID 131713066, compoundHCID 131713067HCID 131713067, compound

Product 1

HCID 131713065HCID 131713065, compoundYield 110.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6 g of L-phenylalanine p-xylenesulfonate, 60 ml of 97% formic acid, 0.85 g of DL-phenylalanine (0.3 mole per mole of L-phenylalanine p-xylenesulfonate) and 0.36 ml of salicylaldehyde (0.2 mole per mole of L-phenylalanine p-xylenesulfonate) were stirred at 100° C. for 4 hours. After the reaction, 1.14 g of p-xylenesulfonic acid dihydrate was dissolved in the mixture, and said mixture was condensed to dryness. 40 ml of acetone were added to the mixture, and said mixture was ice-cooled. The crystalline precipitates were collected by filtration, whereby 6.64 g of DL-phenylalanine p-xylenesulfonate were obtained.

Workup

  1. dissolutionwas dissolved in the mixture
  2. customcondensed to dryness
  3. temperaturecooled
  4. customThe crystalline precipitates
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-176b2e63946d4f2985d6dbf4247ea409
Source dataset
uspto-grants-1983_08
Patent number
US04401820

Reaction notes

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