Succinic anhydride → HCID 86754502, compound

HRID 651854Notes

Reaction equation

HRID 651854 reaction equation
C(N(CC)CC)C.S(O)(O)(=O)=O.[CH:13]1[C:29]2[CH2:28][C@H:27]3[N:30]([CH2:32][CH2:33][C@@:19]45[C@H:26]3[CH:25]=[CH:24][C@H:22]([OH:23])[C@@H:20]4[O:21][C:17]([C:18]=25)=[C:15]([OH:16])[CH:14]=1)[CH3:31].[C:34]1(=[O:40])[O:39][C:37](=[O:38])[CH2:36][CH2:35]1.CC[OH:43].O>CN(C=O)C>[CH:13]1[C:29]2[CH2:28][C@H:27]3[N:30]([CH2:32][CH2:33][C@@:19]45[C@H:26]3[CH:25]=[CH:24][C@H:22]([OH:23])[C@@H:20]4[O:21][C:17]([C:18]=25)=[C:15]([OH:16])[CH:14]=1)[CH3:31].[C:34]([O-:39])(=[O:40])[CH2:35][CH2:36][C:37]([O-:43])=[O:38]

Participants

6

Reactant 4

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 546428064-31-3HCID 19096565Water ethanol

Product 1

HCID 86754502HCID 86754502, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (9.584 ml, 69.45 mmol) was added dropwise to a suspension of morphine sulphate (9.286 g, 27.78 mmol) in dry DMF (140 ml) at 0° C. under nitrogen. After stirring for ten minutes, succinic anhydride (2.781 g, 27.78 mmol) was added portionwise to the reaction. The reaction was monitored by TLC (50% EtOH/H2O) and by analytical HPLC (RtI of Mor-Suc was 5.06′). The reaction was complete in 24 to 48 h and the product precipitated out. The precipitate was filtered and washed with a small volume of cold DMF and THF. Both 1H NMR and HPLC indicated that the product was of sufficient purity for the next reaction (Mor-Suc 6.11 g; 57% yield).

Workup

  1. customthe product precipitated out
  2. filtrationThe precipitate was filtered
  3. washwashed with a small volume of cold DMF and THF
  4. customwas of sufficient purity for the next reaction (Mor-Suc 6.11 g; 57% yield)

Sources & evidence

ORD record
ord-3a3f7c8749c34e2580a253df4cdd4040
Source dataset
uspto-grants-2001_08
Patent number
US06281376B1

Reaction notes

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