Ethyl Acetate → HCID 86625459, compound

HRID 409669Notes

Reaction equation

HRID 409669 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[I: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]([I:23])=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([O:19][CH3:20])[C:18]=1[Cl:4])([CH3:9])([CH3:7])[CH3:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 69181575HCID 69181575, compound

Product 1

HCID 86625459HCID 86625459, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

A solution of sulfurylchloride (0.92 ml, 11.0 mmol, 1.16 equiv) in DCM (20 mL) is added dropwise (30 min) to a cold (−15° C.) solution of (2-iodo-3,5-dimethoxy-phenyl)-carbamic acid tert-butyl ester (3.6 g, 9.49 mmol) in THF (48 ml), under an argon atmosphere. The reaction mixture is allowed to stir for 1 h at −15° C. and then poured onto a mixture of ice/H2O (100 mL), a saturated aqueous solution of NaHCO3 (80 ml), and EtOAc (100 mL). The layers are separated and the aqueous phase is extracted with EtOAc (2×100 mL). The combined organic phase is washed with H2O (3×60 mL) and brine (60 mL), dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM) followed by crystallization from DCM/Hex to afford the title compound. ESI-MS: 411.9, 413.9 [M-H]+, TLC: Rf=0.18 (DCM/Hex, 7:3).

Workup

  1. customThe layers are separated
  2. extractionthe aqueous phase is extracted with EtOAc (2×100 mL)
  3. washThe combined organic phase is washed with H2O (3×60 mL) and brine (60 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography (DCM)
  8. customfollowed by crystallization from DCM/Hex

Sources & evidence

ORD record
ord-d941c9a2a37c452c8b0285b2e267b502
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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