Acetic Acid → HCID 15384846, compound

HRID 1858347Notes

Reaction equation

HRID 1858347 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][C@@H:12]2[O:20][C:21](=[O:28])[CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:29][CH2:30][O:31]C)[CH:4]=[CH:5]2.O.[C:34](O)(=O)C>>[C:30]([O:29][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:18]([CH3:19])[CH2:17][CH2:16][C@:14]45[C:15]=2[C:2]=1[O:1][C@H:13]4[C@@H:12]([O:20][C:21](=[O:28])[CH2:22][C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[CH:11]=[CH:10][C@@H:9]35)(=[O:31])[CH3:34]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 15384845HCID 15384845, compound

Product 1

HCID 15384846HCID 15384846, compoundYield 89.9%

Conditions

Temperature
100 °C

Procedure

A solution of 4,5α-epoxy-3-methoxymethoxy-17-methyl-6α-((2-thienyl)-acetyloxy)-morphinan-7-ene (1.00 g, 2.20 mmol) in glacial acetic acid (30 ml) is mixed with (30 ml) of water and stirred for 5 hours at 100° C. under N2. The solution is evaporated down using a Rotavapor. The residue obtained is purified by flash chromatography (silica gel; mobile phase: CH2Cl2 :MeOH=9:1) and lyophilised in order to obtain 4,5α-epoxy-17-methyl-6α-((2-thienyl)-acetyloxy)-morphinan-7-en-3-ol acetate (0.444 g, 89.9%) as a colourless foam.

Workup

  1. customThe solution is evaporated down
  2. customThe residue obtained
  3. customis purified by flash chromatography (silica gel; mobile phase: CH2Cl2 :MeOH=9:1)

Sources & evidence

ORD record
ord-63bee1dc745e4a838bef22c82f5517ef
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

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