Triethylamine → HCID 18753497, compound

HRID 1838434Notes

Reaction equation

HRID 1838434 reaction equation
C(N(CC)CC)C.Br.[NH2:9][CH:10]1[CH2:15][CH2:14][O:13][C:11]1=[O:12].[O:16]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[O:16]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][C:11]2=[O:12])(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 73508Homoserine lactone hydrobromideHCID 27947564-Phenoxybenzene-1-sulfonyl chloride

Product 1

HCID 18753497HCID 18753497, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (20.0 ml, 143.9 mmol) was added to a suspension of α-amino-γ-butyrolactone hydrobromide (7.28 g, 40.0 mmol) in dichloromethane (80 ml), and then 20 minutes were spent in adding dropwise a solution of 4-phenoxybenzenesulfonyl chloride (11.0 g, 40.9 mmol) in dichloromethane (40 ml) to the mixture with ice-cooling. After this mixture was stirred at room temperature for 2 hours, the solvent of the reaction mixture was evaporated under reduced pressure. The residue was acidified with water and hydrochloric acid (1N), and then extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=2/1 as the eluant to give the title compound (8.74 g, yield 73%) as a white powder.

Workup

  1. custom20 minutes
  2. temperaturecooling
  3. customthe solvent of the reaction mixture was evaporated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-fb2d5ccdde504e69a02f2942a317ac65
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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