Benzyl Bromide → HCID 131720958, compound

HRID 2230012Notes

Reaction equation

HRID 2230012 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][CH:5]=1.[CH2:20]([Br:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH2:7][N:8]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=1.[BrH:27]

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 2734500Boc-3-(3-pyridyl)-D-Ala-OH

Product 1

HCID 131720958HCID 131720958, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Boc-D-Pal (1.36 g, 6.0 mmol) was suspended in 60 ml of acetonitrile. Benzyl bromide (about 50 mmol) was added and the mixture was warmed to 50° C. on a water bath. A cleasr solution resulted, and was stirred at room temperature for 16 hours. A white precipitate formed; TLC after 17 hours showed some starting remaining starting material; stirring continued for a total of 5 days, when the reaction was complete. The solvent was evaporated under reduced pressure, and the residue recrystallized from EtOHlethyl acetate. Yield: 85%; m.p. 166-170° C.

Workup

  1. customA cleasr solution resulted
  2. customA white precipitate formed
  3. waitTLC after 17 hours showed
  4. stirringstirring
  5. customcontinued for a total of 5 days, when
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue recrystallized from EtOHlethyl acetate

Sources & evidence

ORD record
ord-226de0ae772d44d286217744bb7b388c
Source dataset
uspto-grants-2002_07
Patent number
US06423686B1

Reaction notes

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