Potassium Carbonate → HCID 131733842, compound

HRID 708527Notes

Reaction equation

HRID 708527 reaction equation
CS(O[C@@H:6]([C:8]#[CH:9])[CH3:7])(=O)=O.[C:10]([O:14][C:15](=[O:21])[NH:16][CH2:17][CH2:18][CH2:19][NH2:20])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:7][C@H:6]([NH:20][CH2:19][CH2:18][CH2:17][NH:16][C:15](=[O:21])[O:14][C:10]([CH3:12])([CH3:11])[CH3:13])[C:8]#[CH:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 11105518HCID 11105518, compound

Product 1

HCID 131733842HCID 131733842, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of (R)-but-3-yn-2-yl methanesulfonate (2189 mg, 14.77 mmol) in ACN (10 ml) was added dropwise to a suspension of tert-butyl(3-aminopropyl)carbamate (2831 mg, 16.25 mmol) and potassium carbonate (2446 mg, 17.72 mmol) in ACN (50 ml). The reaction mixture was stirred at room temperature for 24 h, whereupon the slurry was filtered and the filtrate was concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 0-8%) to afford the title compound (570 mg, 17%) as a light orange oil. LCMS: R=0.43 min, m/z=227.0 (M+1) Method 2m_acidic.

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 0-8%)

Sources & evidence

ORD record
ord-027580366bb8494ab3d2960cb8ee2a08
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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