Hydrochloric Acid → HCID 86608543, compound

HRID 15391

Reaction equation

HRID 15391 reaction equation
Cl.[NH2:2][C@H:3]([C:11]([NH2:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.[C:32](O)(=[O:36])[C:33]([CH3:35])=[O:34].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[O:34]=[C:33]([CH3:35])[C:32]([NH:13][C:11](=[O:12])[C@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:2])=[O:36]

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 962WaterHCID 1060Pyruvic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 445694Phenylalanine amideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86608543HCID 86608543, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of HCl.H-Phe-NH2 (1.0 g, 4.98 mmol) in DCM (49 mL) was neutralized with Et3N (0.69 mL, 4.98 mmol) at 4° C. To this mixture were added HOBt.H2O (0.76 g, 4.98 mmol), pyruvic acid (0.52 mL, 7.47 mmol), and EDC.HCl (1.05 g, 5.47 mmol), and the mixture was stirred at 4° C. for 30 min and at room temperature for 2 h. After removal of the solvent in vacuo, the residue was dissolved in AcOEt, successively washed with 10% citric acid, 5% NaHCO3 and saturated NaCl for three times, dried over Na2SO4, and concentrated in vacuo to obtain 0.76 g (65%) of the title compound as a white solid: mp 138-140° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.34 (d, J=8.6 Hz, 1H), 7.52 (s, 1H), 7.24-7.19 (m, 6H), 4.45-4.37 (m, 1H), 3.11 (dd, J=4.2, 13.8 Hz, 1H), 2.96 (dd, J=9.5, 13.8 Hz, 1H), 2.26 (s, 3H); HRMS (EI): m/z 234.1008 (M+) (calcd for C12H14N2O3: 234.1004).

Workup

  1. customAfter removal of the solvent in vacuo
  2. dissolutionthe residue was dissolved in AcOEt
  3. washsuccessively washed with 10% citric acid, 5% NaHCO3 and saturated NaCl for three times
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82938c0f307644878101a56eb92c66f8
Source dataset
uspto-grants-2010_06
Patent number
US07732605B2

Linked notes

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