Acetyl chloride → HCID 11106861, compound

HRID 896793Notes

Reaction equation

HRID 896793 reaction equation
[C:1](Cl)(=O)C.[NH:5]1[CH2:12][CH2:11][CH2:10][C@H:6]1[C:7]([OH:9])=[O:8].CCN(CC)CC.[CH:20]1[CH:25]=[CH:24][C:23]([CH2:26]Br)=[CH:22][CH:21]=1>CO>[CH3:1][O:8][C:7](=[O:9])[C@@H:6]1[CH2:10][CH2:11][CH2:12][N:5]1[CH2:26][C:23]1[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 145742L-Proline

Product 1

HCID 11106861HCID 11106861, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetylchloride (9.26 mL, 130.28 mmol) was added dropwise to a stirred and cooled (0° C.) solution of (S)-proline (5 g, 43.42 mmol) in MeOH (86 mL). After the addition, the ice bath was removed and the stirring was continued for 15 h at room temperature. The solvent was then evaporated and the residual oil redissolved in dry CH3CN (70 mL). Et3N (18 mL, 130 mmol) and BnBr (6.20 mL, 52.10 mmol) were added to obtain a white suspension. After 12 h of stirring at room temperature, the CH3CN was evaporated, and the residue was partitioned between saturated NH4Cl (200 mL) and Et2O (200 mL). The phases were separated, the aqueous layer was extracted with Et2O (40 mL×2), and the combined organic phases were washed with water and brine, dried (MgSO4), and concentrated. The residue was purified over silica gel using 5 to 10% EtOAc/pet ether to give a clear oil (6.37 g, 69%): 1H NMR (300 MHz, CDCl3) δ 1.70-2.20 (m, 4H), 2.32-2.46 (m, 1H), 3.00-3.10 (m, 1H), 3.20-3.30 (m, 1H), 3.56 (d, J=12.7 Hz, 1H), 3.64 (s, 3H), 3.88 (d, J=12.7 Hz, 1H), 7.25-7.35 (m, 5H). The spectroscopic data agrees with literature values (Corey, E. J., Link, J. O.; J. Org. Chem. 1991, 56, 442).

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. customThe solvent was then evaporated
  4. dissolutionthe residual oil redissolved in dry CH3CN (70 mL)
  5. customto obtain a white suspension
  6. stirringAfter 12 h of stirring at room temperature
  7. customthe CH3CN was evaporated
  8. customthe residue was partitioned between saturated NH4Cl (200 mL) and Et2O (200 mL)
  9. customThe phases were separated
  10. extractionthe aqueous layer was extracted with Et2O (40 mL×2)
  11. washthe combined organic phases were washed with water and brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated
  14. customThe residue was purified over silica gel using 5 to 10% EtOAc/pet ether

Sources & evidence

ORD record
ord-141d420d37f548fcbf908270ebeb0d67
Source dataset
uspto-grants-2005_07
Patent number
US06919456B2

Reaction notes

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