1,2-Dichloroethane → Cocaine

HRID 585418노트

반응식

HRID 585418 반응식
[CH3:1][O:2][C:3]([C@H:5]1[C@@H:12]([O:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:11][C@H:9]2[NH:10][C@@H:6]1[CH2:7][CH2:8]2)=[O:4].Cl.[CH2:23](N(CC)CC)C.C1(=O)OC(=O)CC1.C(Cl)CCl>C(Cl)Cl.O>[CH3:23][N:10]1[C@H:6]2[C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[C@@H:12]([O:13][C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:15])[CH2:11][C@@H:9]1[CH2:8][CH2:7]2

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 3046136Norcocaine hydrochloride

생성물 1

HCID 446220Cocaine

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of norcocaine hydrochloride (1 g, 3.07 mmol), triethylamine (0.86 ml, 6.14 mmol) in methylene chloride (20 ml) is treated with succinic anhydride (614 mg, 6.14 mmol) and the mixture heated at 45.degree. C. overnight, as described in U.S. Pat. No. 5,876,727. The solvents are removed under reduced pressure and the residue purified using silica gel flash chromatography (2:1 chloroform:methanol as the eluent). This gives succinylated norcocaine (1.0 g, 84%) as a thick syrup (3.beta.-(Benzoyloxy)-8-succinoyl-8-azabicyclo[3.2.1]octane-2.beta.-carboxylic acid methyl ester). To a solution of the acid (14 mg, 0.036 mmol) in distilled water (1 ml) at 0.degree. C., EDC (10.4 mg, 0.055 mmol) was added. After 5 minutes a solution of Qβ VLP in PBS (1 ml) is added dropwise and the mixture is allowed to warm to ambient temperature overnight. The conjugate is purified by dialysis against PBS and the degree of conjugation analyzed by mass spectral analysis. The resultant conjugate is used to immunize individuals.

후처리

  1. temperaturethe mixture heated at 45.degree
  2. customovernight
  3. customThe solvents are removed under reduced pressure
  4. customthe residue purified
  5. additionAfter 5 minutes a solution of Qβ VLP in PBS (1 ml) is added dropwise
  6. customThe conjugate is purified by dialysis against PBS

출처 및 근거

ORD 기록
ord-b21e8c0592014cbeb8120e85855bd297
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06932971B2

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