Triethylamine → HCID 15173281, compound

HRID 2037187Notes

Reaction equation

HRID 2037187 reaction equation
[CH3:1][C:2]1([CH3:12])[O:7][CH2:6][C:5]([CH3:11])([C:8]([OH:10])=O)[CH2:4][O:3]1.Cl.[CH3:14][NH:15][O:16][CH3:17].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>O.CN(C=O)C>[CH3:17][O:16][N:15]([CH3:14])[C:8]([C:5]1([CH3:11])[CH2:4][O:3][C:2]([CH3:1])([CH3:12])[O:7][CH2:6]1)=[O:10]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 113557762,2,5-trimethyl-1,3-dioxane-5-carboxylic Acid

Product 1

HCID 15173281HCID 15173281, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,2,5-trimethyl-1,3-dioxane5-carboxylic acid (1.0 g, 5.74 mmol) and DMF (10 mL) were added N,O-dimethylhydroxylamine hydrochloride (0.84 g, 8.6 mmol), 1-hydroxybenzotriazole hydrate (1.32 g, 8.6 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloric acid (1.651 g, 8.61 mmol) and triethylamine (2.39 mL, 17.2 mmol) under nitrogen atmosphere, and the resulting mixture was stirred at room temperature for 3 hours. After the reaction was completed, water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulphate, and concentrated in vacuo to give N-methoxy-N,2,2,5-tetramethyl-1,3-dioxane5-carboxylic acid amid (1.08 g, yield: 86%) as colorless oil.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f3f26661c0e47f4a312664250ab8f91
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

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