4-Phenylbutyric Acid → 1-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-(4-phenylbutanoyloxy)propane

HRID 1268432

Reaction equation

HRID 1268432 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:35][CH2:36][CH2:37][CH2:38][OH:39])(=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[C:40]1([CH2:46][CH2:47][CH2:48][C:49](O)=[O:50])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:16]([O:35][CH2:36][CH2:37][CH2:38][O:39][C:49](=[O:50])[CH2:48][CH2:47][CH2:46][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)(=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 3

HCID 47754-Phenylbutyric AcidHCID 10868DicyclohexylcarbodiimideHCID 103371121-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-hydroxypropane

Product 1

HCID 691997411-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-(4-phenylbutanoyloxy)propane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,3-dicyclohexylcarbodiimide (710 mg, 3.45 mmol) and 4-(N,N-dimethylamino)pyridine (475 mg, 3.9 mmol) in methylene chloride (10 ml) was added to a solution of 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane (1 g, 3 mmol) and 4-phenylbutanoic acid (520 mg, 3.15 mmol) in methylene chloride (15 ml). The resultant mixture was stirred at room temperature under nitrogen until it was complete as indicated by tlc. The mixture was filtered, concentrated and purified by flash chromatography to yield 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-(4-phenylbutanoyloxy)propane.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-4f1ae29995044dbbb1cf97133bf98864
Source dataset
uspto-grants-2003_04
Patent number
US06555700B1

Linked notes

Loading…