Pyridine → HCID 86673199, compound

HRID 1746358Notes

Reaction equation

HRID 1746358 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:28])[CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH3:27].N1C=CC=CC=1.[Cl:35][C:36](Cl)([O:38]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[C:36]([Cl:35])(=[O:38])[O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:28])[CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 72195415HCID 72195415, compound

Product 1

HCID 86673199HCID 86673199, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(4Z,7Z,10Z,13Z,16Z,19Z)—N-(3-Hydroxypropyl)docosa-4,7,10,13,16,19-hexaenamide (3.0 g, 7.8 mmol) was dissolved in 40 mL of CH2Cl2 and pyridine (650 mg, 8.2 mmol) was added. Triphosgene (7.8 mmol) was then added in portions at 0° C. over a period of 15 min. The resulting reaction mixture was stirred at 0° C. until the reaction was completed, as determined by TLC. The solids were removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford 1.5 g of 3-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)propyl carbonochloridate. (43% yield).

Workup

  1. customThe resulting reaction mixture
  2. customThe solids were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-548789829c574a0c908bb66995811ede
Source dataset
uspto-grants-2015_10
Patent number
US09150504B2

Reaction notes

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