Sodium Iodide → HCID 58980844, compound

HRID 1987906Notes

Reaction equation

HRID 1987906 reaction equation
C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[K].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:13]=1[OH:21].Cl[CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29]>CN(C=O)C>[NH2:18][C:16]1[CH:15]=[CH:14][C:13]([O:21][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:12]([O:11][CH3:10])[CH:17]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 767382-Methoxy-4-nitrophenolHCID 3795708N-Boc-2-chloroethylamineHCID 5462222Potassium

Product 1

HCID 58980844HCID 58980844, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of K2CO3 (280 mg, 2 mmol), NaI (700 mg, 5 mmol), the potassium salt of 2-methoxy-4-nitrophenol (1.37 g, 6.6 mmol), and t-butyl 2-chloroethylcarbamate (1.4 g, 8 mmol) in DMF (8 mL) was heated at 90° C. for 6 hr. After dilution with H2O, the mixture was extracted 4× with CH2Cl2. The combined organic layers were washed 2× with aq. K2CO3, then with brine prior to drying over Na2SO4. After removal of the solvent under vacuum, the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether. Pd catalyzed reduction in ethanol as described in step C of Example 6 yielded tert-butyl 2-(4-amino-2-methoxyphenoxy)ethylcarbamate (700 mg) as an off white solid which was carried forward without further purification.

Workup

  1. extractionAfter dilution with H2O, the mixture was extracted 4× with CH2Cl2
  2. washThe combined organic layers were washed 2× with aq. K2CO3
  3. dry with materialwith brine prior to drying over Na2SO4
  4. customAfter removal of the solvent under vacuum
  5. customthe residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2
  6. washto elute 870 mg of nitrophenyl ether
  7. customwas carried forward without further purification

Sources & evidence

ORD record
ord-d6b5c9ac70cc4553bad653c5a4088120
Source dataset
uspto-grants-2009_06
Patent number
US07553836B2

Reaction notes

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