Hydroxyamine hydrochloride → HCID 178453351, compound

HRID 927803Notes

Reaction equation

HRID 927803 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])([CH2:18][CH:19]1[CH2:21][CH2:20]1)[CH3:17])([CH3:12])([CH3:11])[CH3:10]>CCO.O>[C:9]([O:13][C:14](=[O:24])[NH:15][C:16]([C:22](=[NH:23])[NH:7][OH:8])([CH3:17])[CH2:18][CH:19]1[CH2:20][CH2:21]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 65.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium bi carbonate (0.204 g, 2.9 mmol) was dissolved in EtOH (10 mL) and water (10 mL). Hydroxylamine hydrochloride (0.204 g, 2.9 mmol) was added at 25° C. A solution of (cyano-cyclopropylmethyl-methyl-methyl)-carbamic acid tert-butyl ester (3) (0.7 g, 2.67 mmol) in ethanol (5 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 in ethyl acetate (30 mL) and then filtered. The filtrate was concentrated in vacuo. The residue was purified by chromatography (Combi-Flash, 40 g, 5:95 ethyl acetate/n-hexane) to give the title compound (0.45 g, 65%) as white solid; LC-MS (ELSD peak area, ESI) 100%, 258.2 [M+H]+.

Workup

  1. customthe resulting reaction mixture
  2. customAfter evaporation of solvents
  3. dissolutionthe residue was dissolved in ethyl acetate (30 mL)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by chromatography (Combi-Flash, 40 g, 5:95 ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-dff464036cd14538b79349af860c7f7d
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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