Benzyl Bromide → (cis)-1-Benzoyl-4-hydroxy-L-proline, benzyl ester

HRID 1165974Notes

Reaction equation

HRID 1165974 reaction equation
[C:1]([N:9]1[CH2:16][C@@H:15]([OH:17])[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC(C)=O>[C:1]([N:9]1[CH2:16][C@@H:15]([OH:17])[CH2:14][C@H:10]1[C:11]([O:13][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 14750323cis-1-Benzoyl-4-hydroxy-L-proline

Product 1

HCID 14750341(cis)-1-Benzoyl-4-hydroxy-L-proline, benzyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (cis)-1-benzoyl-4-hydroxy-L-proline (7.074 gm, 30.1 mmole) in acetone was treated dropwise with 1,8-diazabicyclo[5.4.0]- undec-7-ene (5.4 ml, 36.1 mmole) while cooling with a water bath. After stirring under argon for 10 minutes, benzyl bromide (4.3 ml, 36.1 mmole) was added dropwise. After stirring for 3 hours at room temperature, an additional aliquot (0.25 ml) of benzyl bromide was added. The reaction was stirred overnight and the acetone removed in vacuo. The residue was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with additional HCl, sodium bicarbonate solution, brine, and dried (sodium sulfate). Filtration, followed by concentration in vacuo afforded a solid which was recrystallized from ethyl acetate. The yield of the title compound was 8.77 gm (90%).

Workup

  1. temperaturewhile cooling with a water bath
  2. stirringAfter stirring for 3 hours at room temperature
  3. stirringThe reaction was stirred overnight
  4. customthe acetone removed in vacuo
  5. customThe residue was partitioned between ethyl acetate and 1N HCl
  6. washThe organic layer was washed with additional HCl, sodium bicarbonate solution, brine
  7. dry with materialdried (sodium sulfate)
  8. filtrationFiltration
  9. concentrationfollowed by concentration in vacuo
  10. customafforded a solid which
  11. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bfc052d595a24d29bcf34149ac30c4de
Source dataset
uspto-grants-1990_03
Patent number
US04912231

Reaction notes

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