Acetic Anhydride → 3-Monoacetylmorphine

HRID 2185870Notes

Reaction equation

HRID 2185870 reaction equation
[CH:1]1[C:17]2[CH2:16][C@H:15]3[N:18]([CH2:20][CH2:21][C@@:7]45[C@H:14]3[CH:13]=[CH:12][C@H:10]([OH:11])[C@@H:8]4[O:9][C:5]([C:6]=25)=[C:3]([OH:4])[CH:2]=1)[CH3:19].[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(=O)(O)[O-].[Na+]>[C:22]([O:4][C:3]1[CH:2]=[CH:1][C:17]2[CH2:16][C@H:15]3[N:18]([CH3:19])[CH2:20][CH2:21][C@:7]45[C:6]=2[C:5]=1[O:9][C@H:8]4[C@@H:10]([OH:11])[CH:12]=[CH:13][C@@H:14]35)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 5288826Morphine

Product 1

HCID 54625043-MonoacetylmorphineYield 100%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A modification of the method of Welsh (1954) was utilized. Morphine free base (1 am, 3.50 mmol) was suspended in saturated sodium bicarbonate solution (50 ml), and to the stirred suspension was added drop-wise an excess of acetic anhydride (1 ml, 10.6 mmol). The resulting solution was extracted with chloroform (6×10 ml) and the combined organic extracts were dried over anhydrous magnesium sulfate. Following filtration the solvent was removed by rotary evaporation under reduced pressure to afford 1.14 gm (100%) of 3O-acetylmorphine as a glassy white amorphous solid. The product was homogeneous by TLC (CHCl3:MeOH (9:1), Rf=0.85). Elemental Analysis Calcd. for C19H21NO4: C, 69.73, H, 6.42; N, 4.28. Found: C, 69.71;, H,6.40; N, 4.32.)

Workup

  1. extractionThe resulting solution was extracted with chloroform (6×10 ml)
  2. dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltration the solvent
  4. customwas removed by rotary evaporation under reduced pressure

Sources & evidence

ORD record
ord-c6f36d4e2edd43abb6b95034ef5afec3
Source dataset
uspto-grants-2002_06
Patent number
US06403602B1

Reaction notes

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