Ethyl orthoformate → HCID 90402436, compound

HRID 1854763Notes

Reaction equation

HRID 1854763 reaction equation
[CH3:1][C:2]([CH3:14])([S:4]([NH:6][C:7]1(/[C:10](=[N:12]/[OH:13])/[NH2:11])[CH2:9][CH2:8]1)=[O:5])[CH3:3].[CH2:15](OC(OCC)OCC)C>CC(O)=O>[O:13]1[CH:15]=[N:11][C:10]([C:7]2([NH:6][S:4]([C:2]([CH3:14])([CH3:1])[CH3:3])=[O:5])[CH2:9][CH2:8]2)=[N:12]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 90402388HCID 90402388, compound

Product 1

HCID 90402436HCID 90402436, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(Z)-1-(1,1-dimethylethylsulfinamido)-N′-hydroxycyclopropanecarboximidamide (1.0 g, 4.6 mmol) in triethoxymethane (6.0 ml, 36 mmol) was treated with AcOH (6 ml) at rt. The reaction was allowed to stir at rt for 16 h. The reaction was concentrated to dryness azeotroping with toluene 3×. The resulting yellow oil which was purified on silica gel (Biotage, EtOAc/hexanes gradient (Rf ˜approximately 2 in 70% EtOAc/Hex) to give the expected product N-(1-(1,2,4-oxadiazol-3-yl)cyclopropyl)-2-methylpropane-2-sulfinamide (340 mg, 1.5 mmol, 33% yield) consistent by LCMS and NMR. LC-MS retention time: 1.06 min; m/z (MH+): 230. 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 10% acetonitrile/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% acetonitrile/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode. 1H NMR (400 MHz, DMSO-d6) δ 9.44 (s, 1H), 6.36 (s, 1H), 1.57-1.51 (m, 1H), 1.45-1.32 (m, 3H), 1.15 (s, 9H).

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. customazeotroping with toluene 3×
  3. customThe resulting yellow oil which was purified on silica gel (Biotage, EtOAc/hexanes gradient (Rf ˜approximately 2 in 70% EtOAc/Hex)

Sources & evidence

ORD record
ord-fba979ca56c642488f7ac98a8b392e4d
Source dataset
uspto-grants-2015_02
Patent number
US08962651B2

Reaction notes

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