Triethylamine → HCID 57971668, compound

HRID 2276984Notes

Reaction equation

HRID 2276984 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O-:10])=O.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH2:43]([O:47][CH:48]([O:50][NH2:51])[CH3:49])[CH:44]([CH3:46])[CH3:45]>C1COCC1.C(Cl)Cl>[CH3:13][O:12][C:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:10])[NH:51][O:50][CH:48]([O:47][CH2:43][CH:44]([CH3:46])[CH3:45])[CH3:49]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7014868HCID 7014868, compoundHCID 9877377HCID 9877377, compound

Product 1

HCID 57971668HCID 57971668, compoundYield 907%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Monomethyl suberate (25.0 g, 13.3 mmol, 1.0 eq) was dissolved in THF (300 mL) and DCM (300 mL). EDC.HCl (25.46 g, 13.3 mmol, 1.0 eq) was added to the stirred solution, followed by HOBt (17.95 g, 13.3 mmol, 1.0 eq) and triethylamine (48.5 mL, 34.5 mmol, 2.6 eq). O-(1-Isobutoxy-ethyl)-hydroxylamine (21.9 mL, 15.9 mmol, 1.2 eq) was added to the viscous solution and the reaction allowed to stir overnight at room temperature. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added and washed with water (250 mL) and brine (200 mL). The organic layer was isolated, dried (MgSO4), filtered and concentrated in vacuo. The product was obtained as a white solid (36.6 g, 91% yield) LCMS purity 88%, m/z 302 (M++H)+. This was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum, DCM (350 mL)
  2. additionwas added
  3. washwashed with water (250 mL) and brine (200 mL)
  4. customThe organic layer was isolated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4569d4b02d824086a5e0d92da6a97dc4
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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