Hydrochloric Acid → L-phenylalanine methyl ester sulfate

HRID 1196152Notes

Reaction equation

HRID 1196152 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[S:14](=[O:18])(=[O:17])([OH:16])[OH:15].[CH3:19]O>>[S:14]([OH:18])([OH:17])(=[O:16])=[O:15].[CH3:19][O:11][C:10](=[O:12])[C@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:1]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1118Sulfuric AcidHCID 6140L-Phenylalanine

Product 1

HCID 20841682L-phenylalanine methyl ester sulfateYield 66.7%

Procedure

The same esterification procedure as in Example 1 was followed with the exception that 165.2 g of L-phenylalanine and 165.2 g of methanol were used and that the hydrochloric acid was replaced with 120.1 g of 98% sulfuric acid. The reaction was conducted at 60° C. for 8 hours, followed by cooling in order to deposit the crystals, which were collected by filtration and then dried to obtain 184.9 g (63.8% yield) of L-phenylalanine methyl ester sulfate having a purity of 95.7% and containing 0.3% of water and 2.4% of L-phenylalanine.

Workup

  1. temperatureby cooling in order
  2. filtrationwere collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-1ab463adca39436ab0eec024eae6ef11
Source dataset
uspto-grants-1992_05
Patent number
US05113009

Reaction notes

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