Hydroxylamine → HCID 90402388, compound

HRID 1854762Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[NH2:7][OH:8].[C:9]([C:11]1([NH:14][S:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])[CH2:13][CH2:12]1)#[N:10]>CCO>[CH3:18][C:17]([CH3:20])([S:15]([NH:14][C:11]1(/[C:9](=[N:7]/[OH:8])/[NH2:10])[CH2:13][CH2:12]1)=[O:16])[CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

Potassium carbonate (4.45 g, 32.2 mmol) and hydroxylamine hydrochlordie (1.1 g, 16 mmol) was added to a stirring solution of N-(1-cyanocyclopropyl)-2-methylpropane-2-sulfinamide (1.5 g, 8.1 mmol) in EtOH (27 ml) at rt. The reaction was heated to 60° C. for 2 h. Then the reaction was allowed to cool to rt. Celite was added and the mixture was filtered through a pad of celite washing with 100 mL of EtOAc. The filtrate was concentrated to give the expected product (Z)-1-(1,1-dimethylethylsulfinamido)-N′-hydroxycyclopropanecarboximidamide (1.7 g, 7.8 mmol, 96% yield) consistent by LCMS. LC-MS retention time: 1.09 min; m/z (MH+): 220. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 3u C18 2.0×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

temperatureto cool to rt
additionCelite was added
filtrationthe mixture was filtered through a pad of celite
washwashing with 100 mL of EtOAc
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-fcd07c681eca4e4ab57e9d9c1bb96539
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962651B2

Reaction notes

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