Phenethylamine → HCID 69230387, compound

HRID 749406Notes

Reaction equation

HRID 749406 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24])=[O:16])([CH3:13])([CH3:12])[CH3:11].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:10]([O:14][C:15](=[O:16])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[O:24])[NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 757711-HydroxybenzotriazoleHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 69230387HCID 69230387, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Phenethylamine (340 μL, 4.3 mmol), 6-tert-butoxycarbonylamino-hexanoic acid (1.0 g, 4.3 mmol) and 1-hydroxybenzotriazole (700 mg, 5.1 mmol) were dissolved under nitrogen in N,N-dimethylformamide and cooled to 0° C. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added and the mixture stirred overnight, allowing to warm to room temperature. The mixture was partitioned between water and isopropyl acetate. The organics were washed with 0.5 M citric acid, then saturated sodium hydrogen carbonate, dried over sodium sulfate and evaporated to dryness. The residue was used without further purification.

Workup

  1. temperatureto warm to room temperature
  2. customThe mixture was partitioned between water and isopropyl acetate
  3. washThe organics were washed with 0.5 M citric acid
  4. dry with materialsaturated sodium hydrogen carbonate, dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was used without further purification

Sources & evidence

ORD record
ord-e49fa567d0684eb48d4a7aab38c51ebe
Source dataset
uspto-grants-2008_07
Patent number
US07402673B2

Reaction notes

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