Hydrogen chloride-ethyl acetate → HCID 118061678, compound

HRID 632816Notes

Reaction equation

HRID 632816 reaction equation
[CH:1]1([CH2:4][N:5]([C:13]2[CH:18]=[C:17]([C:19]3[O:20][CH:21]=[C:22]([C:24](=[O:41])[NH:25][C:26]4[C:27]([N:32]5[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][OH:39])[C:33]5=[O:40])=[N:28][N:29]([CH3:31])[CH:30]=4)[N:23]=3)[CH:16]=[CH:15][N:14]=2)C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.C(OC(=O)C)C.Cl>CO>[CH:1]1([CH2:4][NH:5][C:13]2[CH:18]=[C:17]([C:19]3[O:20][CH:21]=[C:22]([C:24]([NH:25][C:26]4[C:27]([N:32]5[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][OH:39])[C:33]5=[O:40])=[N:28][N:29]([CH3:31])[CH:30]=4)=[O:41])[N:23]=3)[CH:16]=[CH:15][N:14]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 131735468HCID 131735468, compound

Product 1

HCID 118061678HCID 118061678, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl (cyclopropylmethyl)(4-(4-((3-(3-(2-hydroxyethyl)-2-oxoimidazolidin-1-yl)-1-methyl-1H-pyrazol-4-yl)carbamoyl)-1,3-oxazol-2-yl)pyridin-2-yl)carbamate (208 mg), 4M hydrogen chloride ethyl acetate solution (5 mL) and methanol (5 mL) was stirred at 50° C. for 1 hr, the reaction mixture was cooled, and the solvent was evaporated under reduced pressure. The residue was dissolved in water, and the solution was basified with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (130 mg).

Workup

  1. temperaturethe reaction mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-92df99370cc14d628d5e5cc4db30c43c
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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