Ethyl Acetate → HCID 86625458, compound

HRID 409667Notes

Reaction equation

HRID 409667 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6]([O:10][C:11](=[O:24])[NH:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[C:14]=1[CH3:23])([CH3:9])([CH3:8])[CH3:7].C([O-])(O)=O.[Na+].CCOC(C)=O>C(Cl)Cl.C1COCC1>[C:6]([O:10][C:11](=[O:24])[NH:12][C:13]1[C:14]([CH3:23])=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([O:19][CH3:20])[C:18]=1[Cl:4])([CH3:9])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 69181369HCID 69181369, compound

Product 1

HCID 86625458HCID 86625458, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

A solution of sulfurylchloride (6.7 ml, 79.8 mmol, 1.05 equiv) in DCM (140 mL) is added dropwise (75 min) to a cold (−15° C.) solution of (3,5-dimethoxy-2-methyl-phenyl)-carbamic acid tert-butyl ester (20.4 g, 76.3 mmol) in THF (330 ml), under an argon atmosphere. The reaction mixture is allowed to stir for 3 h at −15° C. and then poured onto a mixture of ice/H2O (400 mL), a saturated aqueous solution of NaHCO3 (400 ml), and EtOAc (400 mL). The layers are separated and the aqueous phase is extracted with EtOAc (2×200 mL). The combined organic phase is washed with H2O (3×200 mL) and brine (200 mL), dried (Na2SO4), filtered and concentrated. The residue is purified by trituration in diethyl ether followed by silica gel column chromatography (Hex/acetone, 95:5) to afford the title compound. ESI-MS: 302.2 [MH]+, TLC: Rf=0.13 (Hex/acetone, 9:1).

Workup

  1. customThe layers are separated
  2. extractionthe aqueous phase is extracted with EtOAc (2×200 mL)
  3. washThe combined organic phase is washed with H2O (3×200 mL) and brine (200 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by trituration in diethyl ether

Sources & evidence

ORD record
ord-22c22bad948f446f9cc53048fd682920
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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