1,4-Dioxane-2,6-dione → HCID 86619729, compound

HRID 709336Notes

Reaction equation

HRID 709336 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH2:21])=[N+:2]=[N-:3].[C:22]1(=[O:29])[O:28][C:26](=[O:27])[CH2:25][O:24][CH2:23]1>ClCCl.O>[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH:21][C:26](=[O:27])[CH2:25][O:24][CH2:23][C:22]([OH:29])=[O:28])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 782321,4-Dioxane-2,6-dioneHCID 2189447617-Azido-3,6,9,12,15-pentaoxaheptadecan-1-amine

Product 1

HCID 86619729HCID 86619729, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 17-azido-3,6,9,12,15-pentaoxaheptadecanamine (15 g, 50 mmol) in dichloromethane (100 mL) was added diglycolic anhydride (Acros, 6.4 g, 55 mmol). The reaction mixture was stirred overnight. The reaction was monitored by ESI-MS analysis, and more reagents were added to drive the reaction to completion. The solution was concentrated to give a yellow residue which was dissolved in water (250 mL). The product was isolated from the aqueous phase by continuous extraction with dichloromethane overnight. Drying and evaporation of the solvent gave a yield of 18 g (85%). The product was characterized by ESI-MS analysis (MH+ calculated: 423.20. found 423.4). The product was used in the next step without further purification.

Workup

  1. additionwere added
  2. customthe reaction to completion
  3. concentrationThe solution was concentrated
  4. customto give a yellow residue which
  5. customDrying
  6. customevaporation of the solvent
  7. customgave a yield of 18 g (85%)
  8. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-4321f58755c140b0a4ded1978689a658
Source dataset
uspto-grants-2015_11
Patent number
US09180213B2

Reaction notes

Loading…