2-Aminothiazole → tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-(1,3-thiazol-2-yl)carbamate

HRID 2353701Notes

Reaction equation

HRID 2353701 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C(=O)(OC(C)(C)C)[O:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=O>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:15][C:12]([O:11][C:9]([N:1]([C:2]1[S:3][CH:4]=[CH:5][N:6]=1)[C:9](=[O:8])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:8])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 21552-AminothiazoleHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 59379867tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-(1,3-thiazol-2-yl)carbamateYield 79.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-aminothiazole (5 g, 0.05 mol), (2-methylpropan-2-yl)oxycarbonyl tert-butyl carbonate (27.8 g, 0.15 mol) and DMAP (100 mg) in THF (100 mL) was stirred at reflux overnight. The mixture was allowed to cool and concentrated in vacuo. The residue was chromatographed on silica, eluting with 8% ethyl acetate in hexane, to give the desired material as a white solid (12 g).

Workup

  1. temperatureat reflux overnight
  2. temperatureto cool
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica
  5. washeluting with 8% ethyl acetate in hexane

Sources & evidence

ORD record
ord-457ab25f55914f61a52cbae8174eabb4
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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