Ammonium Chloride → tert-Butyl 2-oxo-2-(thiophen-3-yl)ethylcarbamate

HRID 2042926Notes

Reaction equation

HRID 2042926 reaction equation
CON(C)[C:4](=[O:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[S:16]1[CH:20]=[CH:19][C:18]([Mg]I)=[CH:17]1.[NH4+].[Cl-]>C1COCC1>[O:14]=[C:4]([C:18]1[CH:19]=[CH:20][S:16][CH:17]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateHCID 178506590HCID 178506590, compound

Product 1

HCID 67995722tert-Butyl 2-oxo-2-(thiophen-3-yl)ethylcarbamateYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the Weinreb amide 45 (1.53 g, 7 mmol) in anhydrous THF (10 mL) was added dropwise (over a 10-min period) a solution of thiophen-3-ylmagnesium iodide (0.3 M in THF, 50 mL) under nitrogen atmosphere at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 18 h. The mixture was poured into a saturated NH4Cl solution and extracted with EtOAc. The organic phase was dried over anhydrous MgSO4, filtered and evaporated under vacuum. The residue was further purified by silica column chromatography to provide the titled compound (776 mg, 46%). MNa+264.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was further purified by silica column chromatography

Sources & evidence

ORD record
ord-08bd0cdb854141ca9fb604c79b258954
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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