Triethylamine → HCID 9992082, compound

HRID 601628Notes

Reaction equation

HRID 601628 reaction equation
CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[NH:30]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31][CH2:32][C:33]([OH:35])=O.[C:43]([NH:46][NH2:47])(=[O:45])[CH3:44]>C(Cl)Cl.O>[C:39]([O:38][C:36](=[O:37])[NH:30][CH2:31][CH2:32][C:33]([NH:47][NH:46][C:43](=[O:45])[CH3:44])=[O:35])([CH3:42])([CH3:41])[CH3:40]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 14039AcetohydrazideHCID 757711-HydroxybenzotriazoleHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 9992082HCID 9992082, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

EDCI.HCl (3.05 g, 15.95 mmol), HOBt (1.66 g, 12.27 mmol) and triethylamine (2.22 ml, 15.95 mmol) are added to a stirred solution of BOC-β-Ala-OH (2.32 g, 12.27 mmol) in DCM (60 ml). After stirring for 30 min at 0° C. acetic acid hydrazide (1.0 g, 13.5 mmol) is added in one portion. The reaction mixture is stirred at 0° C. for 1 hour. The reaction is diluted with water and extracted several times with DCM. The organic extract is dried (MgSO4) and the solvent is removed to give an oil. Purification by chromatography on silica, eluting with EtOAc increasing to EtOAc:EtOH 10:1, affords the titled compound.

Workup

  1. additionis added in one portion
  2. extractionextracted several times with DCM
  3. extractionThe organic extract
  4. dry with materialis dried (MgSO4)
  5. customthe solvent is removed
  6. customto give an oil
  7. customPurification by chromatography on silica
  8. washeluting with EtOAc increasing to EtOAc:EtOH 10:1

Sources & evidence

ORD record
ord-29e64feb3c504841bab2d3d246281422
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Reaction notes

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