Stearyl Alcohol → HCID 53888843, compound

HRID 1761358Notes

Reaction equation

HRID 1761358 reaction equation
C(O)CCCCCCCCCCCCCCCCC.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([OH:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1.[CH2:31]([O:49][C:50](=[O:54])[C@H:51]([CH3:53])[NH2:52])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48].[OH-].[Na+]>C1C=CC=CC=1>[C:20]1([CH3:30])[CH:21]=[CH:22][C:23]([S:26]([OH:29])(=[O:27])=[O:28])=[CH:24][CH:25]=1.[CH2:31]([O:49][C:50](=[O:54])[C@H:51]([CH3:53])[NH2:52])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48].[CH2:31]([O:49][C:50](=[O:54])[C@H:51]([CH3:53])[NH2:52])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]

Participants

6

Reactant 3

HCID 8221Stearyl AlcoholHCID 14798Sodium HydroxideHCID 86742966HCID 86742966, compound

Product 2

HCID 53888843HCID 53888843, compoundYield 94.4%HCID 86742966HCID 86742966, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

L-Alanine stearyl 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 11.4 g (0.06 mole) of stearyl alcohol was used in place of myristyl alcohol. The resulting L-alanine stearyl ester p-toluenesulfonate was dissolved again in 200 ml of benzene, and this solution was treated three times with 300-ml portions of 0.4N 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, there was obtained 16.15 g (94.4% yield) of purified free L-alanine stearyl ester in the form of an oily material.

Workup

  1. washwashed thoroughly with water
  2. washAfter washing with water
  3. customthe benzene layer was isolated
  4. dry with materialdried overnight over anhydrous sodium sulfate
  5. customAfter drying
  6. filtrationthe benzene layer was filtered
  7. customthe resulting benzene solution was evaporated
  8. customto remove the solvent

Sources & evidence

ORD record
ord-173e5382cf6640c292762c248aeea9f7
Source dataset
uspto-grants-1989_05
Patent number
US04826818

Reaction notes

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