Cetyl Alcohol → HCID 13747077, compound

HRID 1761356Notes

Reaction equation

HRID 1761356 reaction equation
C(O)CCCCCCCCCCCCCCC.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24]([OH:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1.[CH2:29]([O:45][C:46](=[O:50])[C@H:47]([CH3:49])[NH2:48])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].[OH-].[Na+]>C1C=CC=CC=1>[C:18]1([CH3:28])[CH:19]=[CH:20][C:21]([S:24]([OH:27])(=[O:25])=[O:26])=[CH:22][CH:23]=1.[CH2:29]([O:45][C:46](=[O:50])[C@H:47]([CH3:49])[NH2:48])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].[CH2:29]([O:45][C:46](=[O:50])[C@H:47]([CH3:49])[NH2:48])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

6

Reactant 3

HCID 2682Cetyl AlcoholHCID 14798Sodium HydroxideHCID 86742965HCID 86742965, compound

Product 2

HCID 13747077HCID 13747077, compoundYield 94.8%HCID 86742965HCID 86742965, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

L-Alanine cetyl ester p-toluenesulfonate was synthesized in the same manner as described in Example 18 for the synthesis of an L-alanine alkyl ester p-toluenesulfonate, except that 13.3 g (0.055 mole) of cetyl alcohol was used in place of myristyl alcohol. The resulting L-alanine cetyl ester p-toluenesulfonate was dissolved again 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, there was obtained 14.86 g (94.8% yield) of purified free L-alanine cetyl ester in the form of an oily material. An infrared absorption spectrum of the free L-alanine cetyl ester thus obtained is shown in FIG. 5. In this figure, the peaks 12 and 13 indicate the C=O stretching and C--O stretching vibrations originating from the ester linkage. The peaks 14, 15 and 16 indicate the NH stretching, NH deformation and C--N stretching vibrations, respectively, of a primary amine. The peak 17 indicates the CH deformation vibration.

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-368b7f25a60d4c7fbcc61a57e86cff87
Source dataset
uspto-grants-1989_05
Patent number
US04826818

Reaction notes

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