Hydrochloric Acid → HCID 91618721, compound

HRID 714910Notes

Reaction equation

HRID 714910 reaction equation
C(OC([NH:8][CH2:9][CH:10]([CH3:22])[C:11]([C:20]#[N:21])([CH:17]1[CH2:19][CH2:18]1)[C:12](OCC)=[O:13])=O)(C)(C)C.Cl>C(OCC)(=O)C>[CH:17]1([C:11]2([C:20]#[N:21])[CH:10]([CH3:22])[CH2:9][NH:8][C:12]2=[O:13])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117840591HCID 117840591, compound

Product 1

HCID 91618721HCID 91618721, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To ethyl 4-((tert-butoxycarbonyl)amino)-2-cyano-2-cyclopropyl-3-methylbutanoate (5.3 g) obtained in Step A of Example 357 was added 4 M hydrogen chloride in ethyl acetate (30 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, to a solution of the residue in acetonitrile (150 mL) was added potassium carbonate (9.4 g), and the mixture was stirred at room temperature for 5 hr. The insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.2 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, to a solution of the residue in acetonitrile (150 mL)
  2. additionwas added potassium carbonate (9.4 g)
  3. stirringthe mixture was stirred at room temperature for 5 hr
  4. customThe insoluble substance was removed by filtration through Celite
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3cb021aefb574d46b7adc8bee386a522
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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