Sodium Iodide → [2-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ylamino)-ethyl]-methyl-carbamic acid tert-butyl ester

HRID 2103347Notes

Reaction equation

HRID 2103347 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16](Cl)[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([O:25][C:26](=[O:32])[N:27]([CH2:29][CH2:30][NH2:31])[CH3:28])([CH3:24])([CH3:23])[CH3:22].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>O.C(#N)C>[C:21]([O:25][C:26](=[O:32])[N:27]([CH2:29][CH2:30][NH:31][CH:16]1[C:17]2[C:12](=[CH:11][C:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])=[CH:19][CH:18]=2)[CH2:13][CH2:14][CH2:15]1)[CH3:28])([CH3:24])([CH3:22])[CH3:23]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2756424N-Boc-N-methylethylenediamineHCID 575267806-Benzenesulfonyl-1-chloro-1,2,3,4-tetrahydro-naphthalene

Product 1

HCID 57804253[2-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ylamino)-ethyl]-methyl-carbamic acid tert-butyl esterYield 46.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

6-Benzenesulfonyl-1-chloro-1,2,3,4-tetrahydro-naphthalene (0.6 g, 1.95 mmol), (2-Amino-ethyl)-methyl-carbamic acid tert-butyl ester (0.512 g, 2.925 mmol), sodium iodide (0.1 g) and potassium carbonate (0.5 g) were added to 50 mL of acetonitrile, and the reaction mixture was refluxed for 120 hours. The reaction mixture was cooled and diluted with 200 mL of water. The aqueous mix was extracted twice with 200 mL of EtOAc, and the combined organic layers were washed with water, brine, and dried over MgSO4. Solvent was removed under reduced pressure, and the resulting oil was eluted through silica gel (medium pressure chromatography) eluting with EtOAc/Hexanes 20%/80%. Removal of solvent under reduced pressure afforded 0.4 g (0.9 mmol, 46%) of [2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ylamino)-ethyl]-methyl-carbamic acid tert-butyl ester as an oil. MS: 446 (M+H)+.

Workup

  1. temperaturethe reaction mixture was refluxed for 120 hours
  2. temperatureThe reaction mixture was cooled
  3. additionThe aqueous mix
  4. extractionwas extracted twice with 200 mL of EtOAc
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried over MgSO4
  7. customSolvent was removed under reduced pressure
  8. washthe resulting oil was eluted through silica gel (medium pressure chromatography)
  9. washeluting with EtOAc/Hexanes 20%/80%
  10. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-87c99ece0f5a43d68fab139c7bdad5ee
Source dataset
uspto-grants-2009_08
Patent number
US07576103B2

Reaction notes

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