Diethyl Ether → HCID 10635280, compound

HRID 1587598Notes

Reaction equation

HRID 1587598 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[OH-].[Na+].C(OCC)C.[C:17](Cl)(=[O:26])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[O:26]=[C:17]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6106L-LeucineHCID 14798Sodium HydroxideHCID 64801Benzenepropanoyl chloride

Product 1

HCID 10635280HCID 10635280, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

L-Leucine (7.87 g, 60 mmol) was dissolved in a solution of sodium hydroxide (4.8 g, 120 mmol) in water (40 ml, 1.5M). Diethyl ether (40 ml) was added. The mixture was cooled in an ice bath and while stirring rapidly, hydrocinnamoyl chloride (10.1 g, 8.92 ml, 60 mmol) was added dropwise over a period of 30 minutes. The ice bath was removed and the mixture was stirred at room temperature 2 hours, maintaining a slightly basic pH by periodic addition of small amounts of 1N sodium hydroxide solution. The layers were separated. The ether layer was reextracted with 1N sodium hydroxide solution. The combined aqueous layers were washed once with ether and then acidified with concentrated hydrochloric acid. The product was extracted into chloroform, dried over magnesium sulfate, and freed of solvent in vacuo leaving a white solid (13.36 g). This material was recrystallized from ethyl acetate (65 ml) to give 8.37 g of the title B compound (53%), m.p. 129°-130° C. [α]D =-41.3° (c=1.3, MeOH).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customThe ice bath was removed
  3. stirringthe mixture was stirred at room temperature 2 hours
  4. temperaturemaintaining a slightly basic pH
  5. additionby periodic addition of small amounts of 1N sodium hydroxide solution
  6. customThe layers were separated
  7. washThe combined aqueous layers were washed once with ether
  8. extractionThe product was extracted into chloroform
  9. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-6663cf4ba3a94418aa53d3784a2c4fb7
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

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