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

HRID 887963Notes

Reaction equation

HRID 887963 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 over night. 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-36c739fa02dc41c0b83c6e3a4da078e0
Source dataset
uspto-grants-2012_08
Patent number
US08247534B2

Reaction notes

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