Triethylamine → N-methoxy-N-methyl-3-oxocyclobutanecarboxamide

HRID 707350Notes

Reaction equation

HRID 707350 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.Cl.[CH3:10][O:11][NH:12][CH3:13].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl.O>[CH3:10][O:11][N:12]([CH3:13])[C:6]([CH:4]1[CH2:3][C:2](=[O:1])[CH2:5]1)=[O:8]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 86634348N-methoxy-N-methyl-3-oxocyclobutanecarboxamideYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-oxo-cyclobutanecarboxylic acid (2.28 g, 20.0 mmol), O,N-dimethyl-hydroxylamine hydrochloride (1.94 g, 20.0 mmol), 1-hydroxybenzotriazole (2.99 g, 22.0 mmol), (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (4.22 g, 22.0 mmol) and triethylamine (4.04 g, 40.0 mmol) in dichloromethane (50 mL) was stirred at room temperature for 24 hours. The mixture was diluted with water (30 mL), and extracted with dichloromethane (2×30 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), and dried over sodium sulfate. The filtrate was evaporated in vacuo and the residue was purified by silica chromatography to provide N-methoxy-N-methyl-3-oxocyclobutanecarboxamide (2.68 g, 17.0 mmol, yield: 85%).

Workup

  1. extractionextracted with dichloromethane (2×30 mL)
  2. washThe combined organic extracts were washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-f645a08471ea44f3b558b89226ec050e
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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