1-Piperazinecarboxylic acid, ethyl ester → HCID 22184879, compound

HRID 348088Notes

Reaction equation

HRID 348088 reaction equation
[C:1]([CH2:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:6])(O)=[O:2].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[CH2:54]([O:56][C:57]([N:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1)=[O:58])[CH3:55]>C(Cl)Cl.C(OCC)(=O)C>[CH2:54]([O:56][C:57]([N:59]1[CH2:60][CH2:61][N:62]([C:1]([CH2:4][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:6])=[O:2])[CH2:63][CH2:64]1)=[O:58])[CH3:55]

Participants

8

Reactant 5

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22184872HCID 22184872, compound

Product 1

HCID 22184879HCID 22184879, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[carboxymethylcarbonyl][(1,1-dimethylethoxycarbonyl)methyl]aminonaphthalene (270 mg, 0.78 mmol) in CH2Cl2 (50 mL) was added triethylamine (0.33 mL, 2.36 mmol) and 1-hydroxybenzotriazole (HOBT) (128 mg, 0.91 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI) (238 mg, 1.23 mmol). After 5 minutes, 1-ethoxycarbonylpiperazine (0.12 mL, 0.78 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was evaporated in vacuo to afford an oil, which was dissolved in ethyl acetate, and washed with saturated NaHCO3, 1M NaHSO4 and brine. The organic layer was evaporated in vacuo and the crude product was purified by flash column to afford 2-[((4-(ethoxycarbonyl)piperazin-1-yl)carbonylmethyl)carbonyl][(1,1-dimethylethoxycarbonyl)methyl]aminonaphthalene (147 mg).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto afford an oil, which
  3. washwashed with saturated NaHCO3, 1M NaHSO4 and brine
  4. customThe organic layer was evaporated in vacuo
  5. customthe crude product was purified by flash column

Sources & evidence

ORD record
ord-cbaf85faec6e4838af22a84f69f440ac
Source dataset
uspto-grants-2007_02
Patent number
US07176207B2

Reaction notes

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