Reaction #1885031

ord-8df241f09b544a7ea0c1387d9cd3e2a2

Reaction equation

CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)ON1C(=O)CCC1=O
Boc-Phe-OSu
COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
oxycodone
[Li][N]([Si](C)(C)C)[Si](C)(C)C
LiN(TMS)2
→
COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314.N[C@@H](Cc1ccccc1)C(=O)O
Phe Oxycodone

Reactants

CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)ON1C(=O)CCC1=O
Boc-Phe-OSu
COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
oxycodone
[Li][N]([Si](C)(C)C)[Si](C)(C)C
LiN(TMS)2

Reagents

None

Solvents

C1CCOC1
tetrahydrofuran

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherquenched with water and solvents
  2. 2
    Otherremoved
  3. 3
    Otherwas purified

Procedure

To a solution of oxycodone-freebase (1.0 eq) in tetrahydrofuran (THF) (10 ml/mmol) was added LiN(TMS)2 (3.5 eq). After 5 minutes, Boc-Phe-OSu (3.5 eq) was added. The reaction was stirred at ambient temperatures for 18 hours, quenched with water and solvents removed. Crude protected product was purified using reverse-phase HPLC. Deprotection occurred with 4N HCl in dioxane (20 ml/mmol) to obtain Phe-Oxycodone.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08343927B2uspto-grants-2013_01