Pyridine → (6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-19-yl (3-hydroxypropyl)(methyl)carbamate

HRID 537839Notes

Reaction equation

HRID 537839 reaction equation
ClC([O:4][C:5](Cl)(Cl)Cl)=O.[CH2:9]([CH:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39]/[CH:40]=[CH:41]\[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[OH:28])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].N1C=CC=CC=1.[CH3:53][NH:54][CH2:55][CH2:56][CH2:57][OH:58]>CCOCC>[OH:58][CH2:57][CH2:56][CH2:55][N:54]([CH3:53])[C:5](=[O:4])[O:28][CH:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39]/[CH:40]=[CH:41]\[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10426DiphosgeneHCID 101489863-(Methylamino)-1-propanolHCID 44468963Dlin-MeOH

Product 1

HCID 86684845(6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-19-yl (3-hydroxypropyl)(methyl)carbamateYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of trichloromethyl chloroformate (340 μL, 2.8 mmol) in anhydrous Et2O (5 mL) was cooled (−15° C.) and treated with a solution of dilinoleyl methanol (1.0 g, 1.9 mmol) and pyridine (230 μL, 2.8 mmol) in Et2O (5 mL). After stirring (1 h) the reaction mixture was filtered through a frit and the filtrate was added, dropwise, to a cool (0° C.) solution of 3-methylamino-propan-1-ol (1.1 mL, 11.3 mmol) in Et2O (5 mL). After stirring (5 min) the reaction mixture was filtered and concentrated. The crude material was subjected to chromatography (12%→20% EtOAc-hexanes) to yield (6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-19-yl (3-hydroxypropyl)(methyl)carbamate (960 mg, 79%) as a colorless oil. Rf 0.17 (10% EtOAc-hexanes), FW 644.07, C42H77NO3.

Workup

  1. filtrationwas filtered through a frit
  2. additionthe filtrate was added
  3. stirringAfter stirring (5 min) the reaction mixture
  4. filtrationwas filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5441f09cc7734d0c9ac3b68299605bcb
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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