Triethylamine → HCID 67342329, compound

HRID 1673385Notes

Reaction equation

HRID 1673385 reaction equation
C(N(CC)CC)C.[CH2:8]([S:15](Cl)(=[O:17])=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:19][C:20]1[CH:32]=[C:31]([CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:30]=[CH:29][C:21]=1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:8]([S:15]([NH:19][C:20]1[CH:32]=[C:31]([CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:30]=[CH:29][C:21]=1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])(=[O:17])=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

Product 1

HCID 67342329HCID 67342329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.082 mL of triethylamine, 39 mg of benzylsulfonyl chloride and 2.0 mL of methylene chloride were added to 1.0 mL of methylene chloride solution containing 50 mg of tert-butyl 2-amino-4-phenethylbenzoate at room temperature and stirred at the same temperature for 2 hours. 380 mg of aminomethylated polystyrene was added to she reaction mixture and stirred at room temperature overnight. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1] to obtain tert-butyl 2-(benzylsulfonamido)-4-phenethylbenzoate.

Workup

  1. stirringstirred at room temperature overnight
  2. customthe organic layer was separated
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-bee9de9513e74dd7956225f66dce1e70
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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