Diethyl Ether → HCID 13036827, compound

HRID 484673Notes

Reaction equation

HRID 484673 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[C@@H:3]([CH3:5])[OH:4].[C:9]1([CH2:15][C:16](Cl)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCOCC>[OH-].[Na+]>[C:9]1([CH2:15][C:16]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[C@@H:3]([CH3:5])[OH:4])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6288L-ThreonineHCID 7679Phenylacetyl chloride

Product 1

HCID 13036827HCID 13036827, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

L-Threonine (35.7 g) is dissolved in 1N sodium hydroxide (1 liter) and chilled to -5° to -10° C. To the cold, mechanically stirred solution is added dropwise phenylacetyl chloride (46.3 g). The reaction mixture is stirred for about 16 hours as the temperature rises to 26° C. The mixture is washed with ether, acidified to pH 2 with hydrochloric acid, and extracted with ethyl acetate (two times). The combined extracts are dried over sodium sulfate and concentrated under reduced pressure until crystalline solids form. Ether is added to the mixture and the crystals are collected (34.8 g); melting point 161°-163° C.

Workup

  1. temperaturechilled to -5° to -10° C
  2. customrises to 26° C
  3. washThe mixture is washed with ether
  4. extractionextracted with ethyl acetate (two times)
  5. dry with materialThe combined extracts are dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure until crystalline solids
  7. customform
  8. customthe crystals are collected (34.8 g)

Sources & evidence

ORD record
ord-bc022da9e4834b498fc58523de2ad1c9
Source dataset
uspto-grants-1985_08
Patent number
US04533660

Reaction notes

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