p-Toluenesulfonic acid → HCID 86742967, compound

HRID 1761359Notes

Reaction equation

HRID 1761359 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([OH:20])(=[O:19])=[O:18])=[CH:15][CH:16]=1.[OH-].[Na+]>C1C=CC=CC=1>[C:11]1([CH3:10])[CH:12]=[CH:13][C:14]([S:17]([OH:20])(=[O:18])=[O:19])=[CH:15][CH:16]=1.[CH2:10]([O:8][C:7](=[O:9])[C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[NH2:1])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6106L-Leucine2×HCID 14798Sodium Hydroxide

Product 1

HCID 86742967HCID 86742967, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Proteinaceous Emulsifier 13 was prepared by using L-leucine in place of L-alanine. Specifically, L-leucine myristyl ester p-toluenesulfonate was synthesized in the same manner as described in Example 18 for the synthesis of an L-alanine ester p-toluenesulfonate, except that L-leucine was used in place of L-alanine. The resulting p-toluenesulfonate was dissolved in 200 ml of benzene, and this solution was treated three times with 300-ml portions of 0.1N NaOH. Thereafter, the benzene layer was isolated and washed thoroughly with water. After washing with water, the benzene layer was isolated and dried overnight over anhydrous sodium sulfate. After drying, the benzene layer was filtered and the resulting benzene solution was evaporated to remove the solvent. Thus, purified L-leucine myristyl ester was obtained in the form of an oily material. Using this ester, an enzymatic reaction was carried out in the same manner as in Example 18 to obtain Proteinaceous Emulsifier 13.

Workup

  1. customProteinaceous Emulsifier 13 was prepared
  2. washwashed thoroughly with water
  3. washAfter washing with water
  4. customthe benzene layer was isolated
  5. dry with materialdried overnight over anhydrous sodium sulfate
  6. customAfter drying
  7. filtrationthe benzene layer was filtered
  8. customthe resulting benzene solution was evaporated
  9. customto remove the solvent
  10. customThus, purified L-leucine myristyl ester
  11. customwas obtained in the form of an oily material
  12. customan enzymatic reaction
  13. customto obtain Proteinaceous Emulsifier 13

Sources & evidence

ORD record
ord-e855d838faed4ccfa22d27b4f6ad6452
Source dataset
uspto-grants-1989_05
Patent number
US04826818

Reaction notes

Loading…