Hydrochloric Acid → HCID 58370309, compound

HRID 2075533Notes

Reaction equation

HRID 2075533 reaction equation
C[O:2][C:3](=[O:32])[C:4]([CH3:31])([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)=[O:8])[CH3:5].Cl>CO.[OH-].[Na+]>[CH3:31][C:4]([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[NH:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:25][CH:26]=1)=[O:8])([CH3:5])[C:3]([OH:32])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66701256HCID 66701256, compound

Product 1

HCID 58370309HCID 58370309, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

140 mg 2-methyl-2-{[1-(4-trifluoromethyl-benzylamino)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester in 2 ml methanol and 1 ml 1M aqueous sodium hydroxide solution was refluxed for 0.5 h. The reaction was acidified with 2 M hydrochloric acid, and the precipitated product was collected by filtration, dissolved in ethyl acetate, dried over sodium sulphate, filtrated, concentrated in vacuo, and the resulting crude product was purified by silica gel chromatography to yield 0.09 g 2-methyl-2-{[1-(4-trifluoromethyl-benzylamino)-naphthalene-2-carbonyl]-amino}-propionic acid.

Workup

  1. filtrationthe precipitated product was collected by filtration
  2. dissolutiondissolved in ethyl acetate
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customthe resulting crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2a8d8b2672d64e5bbbfd1df1fa21bec1
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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