1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68709601, compound

HRID 1927796Notes

Reaction equation

HRID 1927796 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([NH2:22])=[O:21].O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]([CH2:9][C:10]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([NH2:22])=[O:21])=[O:12])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 12707183(S)-Pyrrolidine-2-carboxamide monohydrochlorideHCID 23033833N-(tert-Butoxycarbonyl)-N-(2-methylpropyl)glycine

Product 1

HCID 68709601HCID 68709601, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Nα-(tert-Butyloxycarbonyl)-Nα-(2-methylpropyl) glycine (360 mg, 1.56 mmol) was dissolved in CH2Cl2/DMF (9:1, 20 ml). The solution was cooled to 0° C., L-prolinamide hydrochloride (282 mg, 1.87 mmol), 1-hydroxybenzotriazole hydrate (295 mg, 2.18 mmol) and water soluble carbodiimide (358 mg, 1.87 mmol) were added and after 15 min the pH adjusted to pH9 with triethylamine. After 18 h at 0° C. to room temperature the solvent was removed in vacuo and the residue was taken up in ethyl acetate (100 ml). This solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 4% methanol, 94% chloroform, 2% triethylamine) to give a colourless oil identified as the title compound (330 mg, 1.01 mmol, 65%).

Workup

  1. customAfter 18 h at 0° C. to room temperature the solvent was removed in vacuo
  2. washThis solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (eluant: 4% methanol, 94% chloroform, 2% triethylamine)
  6. customto give a colourless oil

Sources & evidence

ORD record
ord-5f091af6728144d296ecc31a6dc7dfd2
Source dataset
uspto-grants-2012_05
Patent number
US08183280B2

Reaction notes

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