2-Chloroethyl methyl ether → HCID 53684166, compound

HRID 2299623Notes

Reaction equation

HRID 2299623 reaction equation
[OH-].[K+].[CH2:3]([N:10]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:11]1[CH2:17][CH2:16][CH2:15][C:14]2[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:13]=2[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:30][O:31][CH2:32][CH2:33]Cl.C(=O)([O-])O.[Na+]>CS(C)=O>[CH2:3]([N:10]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:11]1[CH2:17][CH2:16][CH2:15][C:14]2[CH:18]=[CH:19][C:20]([O:22][CH2:33][CH2:32][O:31][CH3:30])=[CH:21][C:13]=2[CH2:12]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 123162-Chloroethyl methyl etherHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 54315584HCID 54315584, compound

Product 1

HCID 53684166HCID 53684166, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under nitrogen, to dimethylsulfoxide (5 ml) was added potassium hydroxide (34 mg) at room temperature, and the suspension was stirred at the same temperature for 40 minutes. To this one were added N-benzyl-N-(3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-tert-butoxycarbonylamine (200 mg) and 2-chloroethyl methyl ether (55 μl), and the mixture was stirred at room temperature for 4 hours. The resulting mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1 to 5:1) to give N-benzyl-N-[3-(2-methoxyethoxy)-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]-tert-butoxycarbonylamine (213 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1 to 5:1)

Sources & evidence

ORD record
ord-41dcdf0f17654c4b914c10f443343dd1
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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