1-Hydroxybenzotriazole → N-Methoxy-N-methyl-3-(2,2-dimethylpropyl)cyclobutanecarboxamide

HRID 1912067Notes

Reaction equation

HRID 1912067 reaction equation
[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH:4]1[CH2:7][CH:6]([C:8](O)=[O:9])[CH2:5]1.Cl.[CH3:14][NH:15][O:16][CH3:17].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>O.C(N(CC)CC)C.CN(C=O)C>[CH3:17][O:16][N:15]([CH3:14])[C:8]([CH:6]1[CH2:7][CH:4]([CH2:3][C:2]([CH3:12])([CH3:11])[CH3:1])[CH2:5]1)=[O:9]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866750393-(2,2-Dimethylpropyl)cyclobutane-1-carboxylic acid

Product 1

HCID 86675040N-Methoxy-N-methyl-3-(2,2-dimethylpropyl)cyclobutanecarboxamideYield 101%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

3-(2,2-Dimethylpropyl)cyclobutanecarboxylic acid (75.2 g) and DMF (600 mL) were mixed. After an addition of N,O-dimethylhydroxylamine hydrochloride (51.7 g), triethylamine (92.4 mL), HOBt.H2O (81.2 g) and WSC.HCl (101.6 g) to the mixture, the mixture was stirred at RT overnight. Water was poured into the reaction and the mixture was extracted with ethyl acetate/hexane=1/1. The organic layer was washed with 1 N hydrochloric acid, water, aqueous 10 w/v % sodium carbonate and water, then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (95.2 g) as a crude product.

Workup

  1. extractionthe mixture was extracted with ethyl acetate/hexane=1/1
  2. washThe organic layer was washed with 1 N hydrochloric acid, water, aqueous 10 w/v % sodium carbonate and water
  3. dry with materialdried over sodium sulfate
  4. filtrationThe sodium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-891fb7d8c87f4ad0b33122c0bd25cec6
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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