Ethyl Acetate → HCID 68818292, compound

HRID 900362Notes

Reaction equation

HRID 900362 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:18][O:19][C:20](=[O:32])[CH:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][SH:23].C(OCC)(=O)C>CN(C=O)C.CCCCCCC>[CH3:18][O:19][C:20](=[O:32])[C@@H:21]([NH:24][C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:22][S:23][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 660114-Nitrobenzyl bromideHCID 4399784Methyl 2-(((tert-butoxy)carbonyl)amino)-3-sulfanylpropanoate

Product 1

HCID 68818292HCID 68818292, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Procedure

A mixture of 1-bromomethyl-4-nitro-benzene (2.15 g, 9.95 mmol), cesium carbonate (6.49 g, 19.9 mmol) and 2-tert-butoxycarbonylamino-3-mercapto-propionic acid methyl ester (2.46 g, 10.5 mmol) in DMF (25 mL) was stirred at room temperature. Upon completion of the reaction (TLC control: 30% ethyl acetate in heptane), the reaction mixture was quenched with water (50 mL) and extracted with diethyl ether (3×50 mL). The combined extract was washed sequentially with water and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2; 30% ethyl acetate in heptane as eluent) yielded the thioether as an off-white solid.

Workup

  1. customthe reaction mixture was quenched with water (50 mL)
  2. extractionextracted with diethyl ether (3×50 mL)
  3. extractionThe combined extract
  4. washwas washed sequentially with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography (SiO2; 30% ethyl acetate in heptane as eluent)

Sources & evidence

ORD record
ord-02fa0447722e47d98ae3fc819eef5605
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

Loading…