Reaction #1543046

ord-eb9db57701e74dbca243f37811632466

Reaction equation

CC(C)(C)OC(=O)N[C@H](Cc1cccnc1)C(=O)O
Boc-D-Pal
BrCc1ccccc1
Benzyl bromide
→
Br.CC(C)(C)OC(=O)N[C@H](CC1=CN(Cc2ccccc2)CC=C1)C(=O)O
Boc-D-Pal(Bzl) Hydrobromide
Yield 85.0%

Reactants

CC(C)(C)OC(=O)N[C@H](Cc1cccnc1)C(=O)O
Boc-D-Pal
BrCc1ccccc1
Benzyl bromide

Reagents

None

Solvents

CC#N
acetonitrile

Conditions

Temperature
50°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherA clear solution resulted
  2. 2
    OtherA white precipitate formed
  3. 3
    workup.WAITTLC after 17 hours showed
  4. 4
    workup.STIRRINGstirring
  5. 5
    Othercontinued for a total of 5 days, when
  6. 6
    OtherThe solvent was evaporated under reduced pressure
  7. 7
    Otherthe residue recrystallized from EtOH/ethyl acetate

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 clear 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 EtOH/ethyl acetate. Yield: 85%; m.p. 166°-170° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05843901uspto-grants-1998_12