Triethylamine → HCID 57654660, compound

HRID 1175167Notes

Reaction equation

HRID 1175167 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:10][NH2:11])[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.CC(C(Cl)=O)[C:21](Cl)=[O:22].[C:27]([O:30][CH2:31]C)(=[O:29])[CH3:28]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1([CH2:10][NH:11][C:21](=[O:22])[CH2:28][C:27]([O:30][CH3:31])=[O:29])[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10931669MethylmalonylchlorideHCID 45122079Ethyl 1-(aminomethyl)cyclobutanecarboxylate

Product 1

HCID 57654660HCID 57654660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1-Aminomethyl-cyclobutanecarboxylic acid ethyl ester (WO2006/100208) (1.26 g, 8.0 mmol) and triethylamine (0.88 ml, 9.6 mmol) are dissolved in 30 ml dichloromethane (DCM). The solution is cooled to 0° C. and methylmalonylchloride (0.88 ml, 8.0 mmol) in 10 ml DCM is added within 15 minutes. The reaction mixture is stirred for 1 hour at 0° C. followed by 72 hours stirring at room temperature. The reaction mixture is diluted with 400 ml ethyl acetate, and washed with NaHCO3 solution, 1N HCl and brine. Evaporation of the solvent provides the title compound as viscous oil. LC-MS (m/z, ES+): 258 (MH+), retention time: 1.28 mins (LC-MS method 8)

Workup

  1. waitfollowed by 72 hours
  2. stirringstirring at room temperature
  3. washwashed with NaHCO3 solution, 1N HCl and brine
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-098985568970476e837d8877df261dee
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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