Triphenylphosphine → Morphine Oxycodone

HRID 1255983Notes

Reaction equation

HRID 1255983 reaction equation
[Si]([C:8]1([OH:28])[C:21]2[O:22][C@@H:18]3[C@@:19]45[CH2:23][CH2:24][N:25]([CH3:26])[C@@H:13]([C@@H:14]4[CH:15]=[CH:16][C@@H:17]3[OH:27])[CH2:12][C:11]([C:20]5=2)=[CH:10][CH2:9]1)(C(C)(C)C)(C)C.[CH3:29][N:30]1[C@@H:47]2[CH2:48][C:35]3[CH:36]=[CH:37][C:38]([O:50][CH3:51])=[C:39]4[O:40][C@H:41]5[C:42]([CH2:44][CH2:45][C@:46]2([OH:49])[C@:33]5([C:34]=34)[CH2:32][CH2:31]1)=[O:43].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([C@@]12OC3=C(O[SiH](C)C)C=CC4C[C@H]5N(CC[C@]1([C@H]5C=C[C@@H]2O)C=43)C)CCC>C1COCC1>[CH:10]1[C:11]2[CH2:12][C@H:13]3[N:25]([CH2:24][CH2:23][C@@:19]45[C@H:14]3[CH:15]=[CH:16][C@H:17]([OH:27])[C@@H:18]4[O:22][C:21]([C:20]=25)=[C:8]([OH:28])[CH:9]=1)[CH3:26].[CH3:29][N:30]1[C@@H:47]2[CH2:48][C:35]3[CH:36]=[CH:37][C:38]([O:50][CH3:51])=[C:39]4[O:40][C@H:41]5[C:42]([CH2:44][CH2:45][C@:46]2([OH:49])[C@:33]5([C:34]=34)[CH2:32][CH2:31]1)=[O:43]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5284603OxycodoneHCID 1317199733-Tert-butyldimethylsilylmorphineHCID 178440551HCID 178440551, compound

Product 1

HCID 9830161Morphine Oxycodone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-tert-butyldimethylsilylmorphine (1 eq.) and the oxycodone-linker oxime from step 1 (1 eq.) in an anhydrous solvent such as THF (approximately 0.1 M) is added 2 equivalents of diethyl azodicarboxylate (DEAD) and 2 equivalents of triphenylphosphine. The resulting mixture is stirred at ambient temperature until the 3 -ten-butyldimethylsilylmorphine and/or the oxycodone-linker oxime is consumed, as monitored by TLC or HPLC. The resulting mixture is then subjected to an aqueous work up, and the product is purified by silica gel column chromatography or preparatory HPLC to provide the protected hybrid morphine-oxycodone compound.

Workup

  1. customthe oxycodone-linker oxime is consumed
  2. customthe product is purified by silica gel column chromatography or preparatory HPLC

Sources & evidence

ORD record
ord-fb90de9e9e99472ca2ea8d3735335583
Source dataset
uspto-grants-2013_06
Patent number
US08461171B2

Reaction notes

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