Dicyclohexylcarbodiimide → Fumaric acid mono-(3-methoxy-14-hydroxy-6,7-didehydro-4,5alpha-epoxy-17-methylmorphinan-6-yl) ester

HRID 1766136ノート

反応式

HRID 1766136 の反応式
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].C1CCC(N=C=NC2CCCCC2)CC1.C([O:43][C:44](=[O:50])/[CH:45]=[CH:46]/[C:47](O)=[O:48])(C)(C)C>C(#N)C.CN(C1C=CN=CC=1)C>[CH3:23][O:22][C:10]1[CH:9]=[CH:8][C:7]2[CH2:20][C@H:19]3[N:2]([CH3:1])[CH2:3][CH2:4][C@:5]45[C:6]=2[C:11]=1[O:12][C@H:13]4[C:14]([O:15][C:47](=[O:48])/[CH:46]=[CH:45]/[C:44]([OH:50])=[O:43])=[CH:16][CH2:17][C@@:18]35[OH:21]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 5284603OxycodoneHCID 5797551(2E)-4-(tert-butoxy)-4-oxobut-2-enoic acid

生成物 1

HCID 71171611Fumaric acid mono-(3-methoxy-14-hydroxy-6,7-didehydro-4,5alpha-epoxy-17-methylmorphinan-6-yl) ester

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6342Acetonitrile溶媒2 回

実験手順

Oxycodone free base, 1-1, (13 mg, 0.04 mmol) in 0.5 mL acetonitrile was stirred with TEA (0.034 mL 0.24 mmol) for 30 min at rt. DMAP (15 mg, 0.12 mmol) and DCC (25 mg, 0.12 mmol) were then added to the solution followed by a solution comprised of 4-2 (41 mg, 0.24 mmol) in 1 mL of acetonitrile. The resulting mixture was stirred for 16 h and concentrated under reduced pressure. The resulting residue was stirred with 4 mL of acetone for 30 min, the precipitated DCU removed by filtration, and the acetone removed under reduced pressure. The residue was treated with 0.8 mL of TFA (5 min at rt) to remove the tert-butyl group. The TFA was then removed under reduced pressure and the resulting residue purified by HPLC on a C-18 column eluted with 20% acetonitrile in 0.07% aqueous TFA to yield fraction containing essentially pure 4-3.

後処理

  1. concentrationconcentrated under reduced pressure
  2. stirringThe resulting residue was stirred with 4 mL of acetone for 30 min
  3. customthe precipitated DCU removed by filtration
  4. customthe acetone removed under reduced pressure
  5. additionThe residue was treated with 0.8 mL of TFA (5 min at rt)
  6. customto remove the tert-butyl group
  7. customThe TFA was then removed under reduced pressure
  8. customthe resulting residue purified by HPLC on a C-18 column
  9. washeluted with 20% acetonitrile in 0.07% aqueous TFA
  10. customto yield fraction
  11. additioncontaining essentially pure 4-3

出典と根拠

ORDレコード
ord-da0797d899164f54be529cf52dc9bea0
出典データセット
uspto-grants-2007_06
特許番号
US07230005B2

反応ノート

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