Acetonitrile → HCID 42260685, compound

HRID 469726Notes

Reaction equation

HRID 469726 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3]1.C(#N)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:6]2[C:2](=[O:1])[CH2:3][CH2:4][C@H:5]2[C:7]([OH:9])=[O:8])=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 7405L-Pyroglutamic AcidHCID 742994-Chlorophenylboronic acid

Product 1

HCID 42260685HCID 42260685, compound

Procedure

To a stirred suspension of (S)-5-oxo-pyrrolidine-2-carboxylic acid (775 mg, 6 mmol) in acetonitrile (10 mL) 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) (1.8 mL, 12 mmol) is added at room temperature. After 10 min di-μ-hydroxy-bis[N,N,N′,N′-tetramethylenediamine)-copper (II) chloride (Cu-TMEDA) (300 mg, 0.65 mmol) is added to the clear solution. The bluish green colored mixture is stirred for 10 min and 4-chlorophenylboronic acid (1 g, 6.4 mmol) is added. After 20 h acetonitrile is evaporated in vacuo, the concentrate taken up in ammonium chloride (150 mL) and the aqueous layer is washed with ethyl acetate (3×100 mL). The aqueous layer is cooled in an ice-bath, treated with 1 N sulfuric acid to pH 2 and extracted with ethyl acetate (3×100 mL). Combined organic extracts washed with brine (2×50 mL), dried over anhydrous Na2SO4 and solvent removed in vacuo to give the title compound as an off-white solid. ESI m/z 240 [M+H]+.

Workup

  1. additionis added at room temperature
  2. customAfter 20 h acetonitrile is evaporated in vacuo
  3. washthe aqueous layer is washed with ethyl acetate (3×100 mL)
  4. temperatureThe aqueous layer is cooled in an ice-bath
  5. additiontreated with 1 N sulfuric acid to pH 2
  6. extractionextracted with ethyl acetate (3×100 mL)
  7. washCombined organic extracts washed with brine (2×50 mL)
  8. dry with materialdried over anhydrous Na2SO4 and solvent
  9. customremoved in vacuo

Sources & evidence

ORD record
ord-b2f55eb41a6e4e27b01e6083c3cfc169
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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