L-Phenylalanine → HCID 68899444, compound

HRID 1884804Notes

Reaction equation

HRID 1884804 reaction equation
[CH2:1]([S:11](Cl)(=[O:13])=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[NH2:15][C@H:16]([C:24]([OH:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC.[OH-].[Na+]>[CH2:1]([S:11]([NH:15][C@H:16]([C:24]([OH:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:13])=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 6140L-PhenylalanineHCID 1091071-Decanesulfonyl chloride

Product 1

HCID 68899444HCID 68899444, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of decanesulfonyl chloride (0.8571 g, 3.56 mmol) in ether (7.5 ml) was added to a solution of L-phenylalanine (0.7441 g, 4.40 mmol) in 10 ml of 1.0 N sodium hydroxide and stirred at room temperature overnight. The reaction mixture was extracted with ethyl acetate and the aqueous phase was separated and acidified to pH 1 with 6 N hydrochloric acid. The resulting precipitate was extracted into ethyl acetate and the extract was washed with water and dried with magnesium sulfate. Evaporation of the ethyl acetate gave an oil which crystallized (see Table 1). Yield 0.245 g; FABMS m/z 370(M+H)+, 392(M+Na)+, Calculated for C19H32NO4S, 370.20; C19H31NO4SNa, 392.19.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. customthe aqueous phase was separated
  3. extractionThe resulting precipitate was extracted into ethyl acetate
  4. washthe extract was washed with water
  5. dry with materialdried with magnesium sulfate
  6. customEvaporation of the ethyl acetate
  7. customgave an oil which
  8. customcrystallized (see Table 1)

Sources & evidence

ORD record
ord-e17ef25da8e6442d81d298d0172fbe69
Source dataset
uspto-grants-2004_07
Patent number
US06767718B2

Reaction notes

Loading…