5-Aminovaleric acid → HCID 20531976, compound

HRID 1759356Notes

Reaction equation

HRID 1759356 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[CH2:9](O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O>C1(C)C=CC=CC=1>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 1385-Aminovaleric acidHCID 8221Stearyl AlcoholHCID 85570p-ToluenesulfonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 20531976HCID 20531976, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5.05 gm (43.1 mmole) of 5-aminopentanoic acid, 23.3 gm (86.1 mmole) of stearyl alcohol, and 12.0 gm (63.1 mmole) of p-toluenesulfonic acid monohydrate in 200 ml of toluene was heated at reflux, using a Dean-Stark trap to remove water. After 90 minutes, the solution was allowed to cool to 0° C., giving a heavy gelatinous precipitate. The crude ester was collected, washed thoroughly with toluene, triturated with diethyl ether, and dried in vacuo to give 21.1 gm (38.8 mmole) of fluffy white octadecyl 5-aminopentanoate as the tosylate salt. The ester was sufficiently pure according to nmr spectroscopy (in (CD3)2SO) for subsequent use without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customto remove water
  4. customgiving a heavy gelatinous precipitate
  5. customThe crude ester was collected
  6. washwashed thoroughly with toluene
  7. customtriturated with diethyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-6df66363fc4e42b4b86d5c70159947cb
Source dataset
uspto-grants-1982_07
Patent number
US04340730

Reaction notes

Loading…