Ethyl Acetate → HCID 18536035, compound

HRID 412149Notes

Reaction equation

HRID 412149 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH2:14].ON1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2N=N1.Cl.CN(CCCN=C=NCC)C.[CH3:37][CH2:38][O:39]C(C)=O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:38](=[O:39])[CH2:37][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:14])[CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 18536035HCID 18536035, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-tert-Butyloxycarbonylpiperazine (9.80 g, 52.6 mmol) and 3-(hydroxyphenyl)acetic acid (8.16 g, 152 mmol) in 100 mL of dimethylformamide at 0° C. was added 1-hydroxybenzotriazole hydrate (9.94 g, 73.6 mmol) and 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (13.06 g, 68.3 mmol). The solution was allowed to warm to room temperature. After 30 minutes, the reaction was poured into EtOAc and washed with water, saturated NH4Cl solution, saturated NaHCO3 solution, and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated as a white foam which was used without further purification.

Workup

  1. washwashed with water, saturated NH4Cl solution, saturated NaHCO3 solution, and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was isolated as a white foam which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-94a9c4dc2ffb4ccbb69962a843ef2af6
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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