1,4-Dioxane → HCID 89535947, compound

HRID 571380Notes

Reaction equation

HRID 571380 reaction equation
CS(O[CH2:6][C@@H:7]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)=O.[CH3:22][S-:23].[Na+].O1CCOCC1>CO>[CH3:22][S:23][CH2:6][C@@H:7]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 4378561Sodium methanethiolateHCID 10335849(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl methanesulfonate

Product 1

HCID 89535947HCID 89535947, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

(S)-2-((tert-butoxycarbonyl)amino)-2-phenylethyl methanesulfonate (600 mg, 1.902 mmol) and sodium thiomethoxide (593 mg, 7.61 mmol) were added to a 20 mL microwave tube equipped with mechanical stir bar and charged with Dioxane (10 ml). The reaction was allowed to heat overnight at 45° C. The reaction was poured into 5 mL MeOH and 5 g silica, and the solvents were evaporated in vacuo. The dry-loaded crude product was purified on 50 g SNAP column 10-50% EtOAc/hexanes to provide (S)-tert-butyl (2-(methylthio)-1-phenylethyl)carbamate (387 mg, 1.447 mmol, 76% yield).

Workup

  1. customequipped with mechanical stir bar
  2. customthe solvents were evaporated in vacuo
  3. customThe dry-loaded crude product was purified on 50 g SNAP column 10-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-86801c9302f14a6ba54e1f998403fc75
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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