Hydroxyamine hydrochloride → HCID 178453351, compound

HRID 927821Notes

Reaction equation

HRID 927821 reaction equation
C(=O)(O)[O-].[Na+].Cl.[NH2:7][OH:8].[C:9]([O:13][C:14](=[O:24])[NH:15][C:16]([C:22]#[N:23])([CH3:21])[CH2:17][CH:18]1[CH2:20][CH2:19]1)([CH3:12])([CH3:11])[CH3:10]>O.C(O)C>[C:9]([O:13][C:14](=[O:24])[NH:15][C:16]([C:22](=[NH:23])[NH:7][OH:8])([CH3:21])[CH2:17][CH:18]1[CH2:19][CH2:20]1)([CH3:10])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 71087668(Cyano-cyclopropylmethyl-methyl-methyl)-carbamic acid tert-butyl ester

Product 1

HCID 178453351HCID 178453351, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium bicarbonate (247.52 mg, 2.94 mmol) was dissolved in water (2 mL) and hydroxylamine hydrochloride (204.747 mg, 2.94 mmol) was added. A solution of (1-cyano-2-cyclopropyl-1-methyl-ethyl)-carbamic acid tert-butyl ester (600 mg, 2.69 mmol) in ethanol (10 mL) was added thereto and the resulting reaction mixture was heated at 80° C. for 12 hours. After evaporation of solvents, the residue was dissolved with ethyl acetate (20 mL) and then filtered. The filtrate was concentrated in vacuo. The residue was purified by chromatography (silica gel, 25 g, 3:7 ethyl acetate/n-hexane) to give the title compound (450 mg, 66%) as white solid; LC-MS (UV peak area, ESI) 100%, 258.4 (M+H).

Workup

  1. customthe resulting reaction mixture
  2. customAfter evaporation of solvents
  3. dissolutionthe residue was dissolved with ethyl acetate (20 mL)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by chromatography (silica gel, 25 g, 3:7 ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-ac83339404a84460902da68a13eafd8f
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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