Diethyl Pyrocarbonate → Morphine

HRID 1871832Notes

Reaction equation

HRID 1871832 reaction equation
CCOC(OC(OCC)=O)=O.CCCCCCCC/C=C\CCCCCCCC(OC[C@@H](OC(CCCCCCC/C=C\CCCCCCCC)=O)COP(OCC[N+](C)(C)C)([O-])=O)=O.S(O)(O)(=O)=O.[CH:71]1[C:87]2[CH2:86][C@H:85]3[N:88]([CH2:90][CH2:91][C@@:77]45[C@H:84]3[CH:83]=[CH:82][C@H:80]([OH:81])[C@@H:78]4[O:79][C:75]([C:76]=25)=[C:73]([OH:74])[CH:72]=1)[CH3:89].C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>Cl.O.[Na+].[Cl-]>[CH:71]1[C:87]2[CH2:86][C@H:85]3[N:88]([CH2:90][CH2:91][C@@:77]45[C@H:84]3[CH:83]=[CH:82][C@H:80]([OH:81])[C@@H:78]4[O:79][C:75]([C:76]=25)=[C:73]([OH:74])[CH:72]=1)[CH3:89]

Participants

7

Reactant 4

HCID 3051Diethyl PyrocarbonateHCID 5988SucroseHCID 546428064-31-32×HCID 103503171,2-Dioleoyl-sn-glycero-3-phosphocholine

Product 1

HCID 5288826Morphine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A lipid component containing DEPC, rather than DOPC, was prepared as in Example 1. The first aqueous component contained 17 mg/mL of morphine sulfate (Mallinckrodt Chemical Inc., St. Louis, Mo.) in 10 mM hydrochloric acid, and 0.2, 2.5 or 5.0 w/v % of sucrose as osmotic excipient. The remainder of the steps described in Example 1 were carried out to obtain MVLs containing morphine sulfate suspended in normal saline. The estimated osmolarity (mOsm), percent yield, and drug loading of these formulations are shown in Table 5 below:

Workup

  1. customto obtain MVLs
  2. customThe estimated osmolarity (mOsm), percent yield

Sources & evidence

ORD record
ord-ad2248c683b34b69937f1fa789709725
Source dataset
uspto-grants-2000_08
Patent number
US06106858

Reaction notes

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