Thiophenol → Alanine, N-ethyl-, methyl ester (7CI)

HRID 2243111Notes

Reaction equation

HRID 2243111 reaction equation
[CH2:1]([N:3](S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:4]([CH3:9])[C:5]([O:7][CH3:8])=[O:6])[CH3:2].C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:1]([NH:3][CH:4]([CH3:9])[C:5]([O:7][CH3:8])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 68548246HCID 68548246, compound

Product 1

HCID 53407612Alanine, N-ethyl-, methyl ester (7CI)Yield 31.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 2-[ethyl(2-nitrobenzenesulfonyl)amino]propionate (8.07 g; 25.5 mmol) is dissolved in 250 ml of acetonitrile, and thiophenol (1.12 eq.; 28.7 mmol; 2.93 ml) and K2CO3 (3.25 eq.; 82.9 mmol; 11.45 g) are then added. The reaction medium is stirred overnight at room temperature. The crude product is evaporated to dryness and then taken up in ether. The organic phase is acidified with 1N hydrochloric acid and then washed with water. The aqueous phases are combined and then washed with ether and basified with potassium carbonate. The basic aqueous phase is extracted with ether three times. The three ether phases are washed with water and then with saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated to dryness to give 1.04 g of the expected product.

Workup

  1. customThe crude product is evaporated to dryness
  2. washwashed with water
  3. washwashed with ether and basified with potassium carbonate
  4. extractionThe basic aqueous phase is extracted with ether three times
  5. washThe three ether phases are washed with water
  6. dry with materialwith saturated aqueous sodium chloride solution, dried over sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-32c7055a59564f21b6b042cdd5aa4451
Source dataset
uspto-grants-2010_03
Patent number
US07674803B2

Reaction notes

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