Triethylamine → HCID 53404827, compound

HRID 1177526Notes

Reaction equation

HRID 1177526 reaction equation
ON1C2C=CC=CC=2N=N1.[O:11]=[C:12]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13]1.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:33][NH:34][O:35][CH3:36].C(N(CC)CC)C>C(Cl)Cl>[CH3:36][O:35][N:34]([CH3:33])[C:17]([CH:14]1[CH2:15][CH2:16][C:12](=[O:11])[CH2:13]1)=[O:19]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2277983-Oxocyclopentanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 53404827HCID 53404827, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of 1-hydroxybenzotriazole (7.91 g, 58.5 mmol), 3-oxo-1-cyclopentanecarboxylic acid (5.00 g, 39.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (11.22 g, 58.5 mmol) in 44 mL DCM under nitrogen was added N,O-dimethylhydroxylamine hydrochloride (5.71 g, 58.5 mmol) followed by triethylamine (8.16 mL, 58.5 mmol) in portions. The reaction mixture became warm and was cooled with an ice bath for the remainder of TEA addition, then stirred at ambient temp under nitrogen for 2 d. The reaction mixture was concentrated in vacuo, and taken up in EA (300 mL), washed with water, sat'd aq. Sodium bicarbonate, brine, and the organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo, to give (rac)-N-methoxy-N-methyl-3-oxocyclopentanecarboxamide as a yellow oil which was used without further purification. 1H NMR (400 MHz, CDCl3-d) δ ppm 3.74 (s, 3 H), 3.41-3.61 (m, 1 H), 3.23 (s, 3 H), 2.52-2.64 (m, 1 H), 2.34-2.50 (m, 2 H), 2.08-2.31 (m, 3 H).

Workup

  1. temperatureThe reaction mixture became warm
  2. temperaturewas cooled with an ice bath for the remainder of TEA addition
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. washwashed with water
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7bde6257c4844769b759eb463923e6c9
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

Loading…