Pyridine → 4-(Bis-decyl-carbamoyloxy)-undecanoic Acid hex-3-enyl Ester

HRID 2304960Notes

Reaction equation

HRID 2304960 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([O:11][C:12](=[O:24])[CH2:13][CH2:14][CH:15]([OH:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:6][CH:7]=[CH:8][CH2:9][CH3:10].N1C=CC=CC=1.[CH2:31]([NH:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>C1(C)C=CC=CC=1.O>[CH2:5]([O:11][C:12](=[O:24])[CH2:13][CH2:14][CH:15]([O:23][C:1](=[O:2])[N:41]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:6][CH:7]=[CH:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 6371PhosgeneHCID 14261DidecylamineHCID 541528994-Hydroxy-undecanoic acid hex-3-enyl ester

Product 1

HCID 538307604-(Bis-decyl-carbamoyloxy)-undecanoic Acid hex-3-enyl Ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To 6.20 ml of an ice-cooled 20% solution of phosgene in toluene was slowly added a solution of 3 g 4-hydroxy-undecanoic acid hex-3-enyl ester and 0.93 g pyridine in 3 ml toluene. The reaction mixture was stirred for 16 hours at room temperature. A mixture of 3.48 g didecylamine and 0.93 g pyridine was added and the mixture was stirred for another 16 hours. Water was added and the mixture extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, 2N hydrochloric acid, water, dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed on silica gel to give 2.9 g of a colorless liquid.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for another 16 hours
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium bicarbonate, 2N hydrochloric acid, water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-2df18855ebbb464c88caef83bc410844
Source dataset
uspto-grants-2002_08
Patent number
US06437150B1

Reaction notes

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