Trifluoroacetic acid → HCID 86587522, compound

HRID 982957Notes

Reaction equation

HRID 982957 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([CH2:14][C:15]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]=2[NH:27]CC(OC(C)(C)C)=O)=[O:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:36]([OH:42])([C:38](F)(F)F)=[O:37].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([CH2:14][C:15]([C:17]2[C:26]([CH2:38][C:36]([OH:42])=[O:37])=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]=2[NH2:27])=[O:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 22184879HCID 22184879, compound

Product 1

HCID 86587522HCID 86587522, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[((4-(ethoxycarbonyl)piperazin-1-yl)carbonylmethyl)carbonyl][(1,1-dimethylethoxycarbonyl)methyl]aminonaphthalene (147 mg, 0.30 mmol) in CH2Cl2 (2.0 mL) was added TFA (3.0 mL). The resulting reaction mixture was stirred at ambient temperature for 3 hours. The reaction mixture was evaporated in vacuo to afford an oil, which was diluted with water (15 mL), adjusted to pH 4.5 by saturated NaHCO3, then extracted by ethyl acetate (3×15 mL). The organic layer was evaporated in vacuo to afford 2-[((4-(ethoxycarbonyl)piperazin-1-yl)carbonylmethyl)carbonyl][carboxymethyl]-aminonaphthalene (90 mg) as a solid; NMR (CDCl3) 1.26 (t, 3), 3.24-3.30 (m, 2), 3.35-3.42 (m, 6), 3.57 (m, 2), 4.14 (q, 2), 4.52 (s, 2), 7.48 (d, 1), 7.58 (m, 2), 7.84-7.94 (m, 4) ppm.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was evaporated in vacuo
  3. customto afford an oil, which
  4. extractionextracted by ethyl acetate (3×15 mL)
  5. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-79106535919a4ca4b860fe85b52963da
Source dataset
uspto-grants-2005_03
Patent number
US06861424B2

Reaction notes

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