Water → Thebaine

HRID 840345

반응식

HRID 840345 반응식
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH:16]=[CH:17][C@@H:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].[CH3:23]C(C)([O-])C.[K+].FC(F)(F)S(OC)(=O)=O.O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([O:15][CH3:23])=[CH:16][CH:17]=[C:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1

참가 물질

7

반응물 4

HCID 962WaterHCID 9526Methyl triflateHCID 5459910CodeinoneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 5324289Thebaine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Codeinone (300 mg) was added to a stirred suspension of potassium tert-butoxide (153 mg) in N,N-dimethylformamide (5 ml) at room temperature. After 10 minutes, methyl trifluoromethanesulphonate (164 mg) was added dropwise to the suspension. The solution was stirred for 5 minutes, diluted with ethyl acetate (30 ml), and then poured into water (50 ml). The aqueous phase was removed, and the organic phase was dried with sodium sulphate and evaporated, producing an orange solid. Analysis by HPLC against pure thebaine gave a thebaine content of 10%.

후처리

  1. customThe aqueous phase was removed
  2. dry with materialthe organic phase was dried with sodium sulphate
  3. customevaporated
  4. customproducing an orange solid

출처 및 근거

ORD 기록
ord-d2e322c4d0dd4e6dabaf0efbdbcd0e09
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06365742B1

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