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Succinic anhydride → Salvinorin A

HRID 1509365
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HRID 1509365 반응식
[CH3:1][C@:2]12[C@H:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][C@H:15]([OH:22])[C:13](=[O:14])[C@@H:12]1[C@:11]1([CH3:23])[C@H:5]([C:6]([O:8][C@H:9]([C:24]3[CH:25]=[CH:26][O:27][CH:28]=3)[CH2:10]1)=[O:7])[CH2:4][CH2:3]2.C1(=O)O[C:32](=[O:33])[CH2:31]C1.C1CCN2C(=NCCC2)CC1>ClCCl>[CH3:31][C:32]([O:22][C@@H:15]1[C:13](=[O:14])[C@H:12]2[C@@:2]([CH3:1])([CH2:3][CH2:4][C@@H:5]3[C@:11]2([CH3:23])[CH2:10][C@@H:9]([C:24]2[CH:25]=[CH:26][O:27][CH:28]=2)[O:8][C:6]3=[O:7])[C@H:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:16]1)=[O:33]
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참가 물질

5

반응물 3

HCID 7922Succinic anhydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11440685Salvinorin B

생성물 1

HCID 128563Salvinorin A

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To Salvinorin B (190 mg, 0.487 mmol) and succinic anhydride (112 mg, 2.5 eq) suspended in dichloromethane (5 ml) at 0° C. was added DBU (218 pl, 3 eq) dropwise. The mixture was stirred at 0° C. for 15 mins, washed with 3% citric acid (5 ml), saturated NaHCO3 solution (5 ml) and brine (5 ml). The mixture was dried over sodium sulfate, filtered and evaporated to dryness. The crude residue was purified by column chromatography (silica gel: CH2Cl2 to 5% MeOH in CH2Cl2) to give salvinorin hemisuccinate (130 mg, 54%).

후처리

  1. washwashed with 3% citric acid (5 ml), saturated NaHCO3 solution (5 ml) and brine (5 ml)
  2. dry with materialThe mixture was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude residue was purified by column chromatography (silica gel: CH2Cl2 to 5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-82dd4338f69d45bfb15f0f0965eaa3cd
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09222949B2

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