Water → HCID 58443400, compound

HRID 2067959Notes

Reaction equation

HRID 2067959 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]([C:12]1[CH:13]=[N:14][CH:15]=[C:16](Br)[CH:17]=1)[CH2:9][CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].[CH3:20][S-:21].[Na+].O>C1COCC1>[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([S:21][CH3:20])[CH:17]=1)[CH2:9][CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 58443385HCID 58443385, compound

Product 1

HCID 58443400HCID 58443400, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [1-(5-bromo-pyridin-3-yl)-butyl]-carbamic acid tert-butyl ester (6.3 g, 19 mmol) and sodium thiomethoxide (2.7 g, 38 mmol) in anhydrous THF (27 mL) is heated at 70° C. After 2 hours the reaction is cooled to room temperature and water (200 mL) is added. The resultant mixture is extracted with ethyl acetate (3×200 mL). The combined organic layers are combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue is purified by flash chromatography on silica gel (eluted with 0 to 60% EtOAc/hexanes) to afford [1-(5-methylsulfanyl-pyridin-3-yl)-butyl]-carbamic acid tert-butyl ester (3.9 g, 68%) as a thick light yellow oil.

Workup

  1. extractionThe resultant mixture is extracted with ethyl acetate (3×200 mL)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography on silica gel (eluted with 0 to 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0e5fc82dd21a4027815ca9a1827e739d
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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