Methyl chloroformate → (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl methyl carbonate

HRID 720937

반응식

HRID 720937 반응식
C(N(CC)CC)C.Cl[C:9]([O:11][CH3:12])=[O:10].[CH3:13][C:14]([NH:16][CH:17]1[C:27]2[CH:28]=[C:29]([OH:32])[CH:30]=[CH:31][C:26]=2[C:25]2[C:20](=[CH:21][C:22]([O:37][CH3:38])=[C:23]([O:35][CH3:36])[C:24]=2[O:33][CH3:34])[CH2:19][CH2:18]1)=[O:15]>C1COCC1>[C:9](=[O:10])([O:11][CH3:12])[O:32][C:29]1[CH:30]=[CH:31][C:26]2[C:25]3[C:24]([O:33][CH3:34])=[C:23]([O:35][CH3:36])[C:22]([O:37][CH3:38])=[CH:21][C:20]=3[CH2:19][CH2:18][C@H:17]([NH:16][C:14](=[O:15])[CH3:13])[C:27]=2[CH:28]=1

참가 물질

5

반응물 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 97865N-Acetylcolchicinol

생성물 1

HCID 9953634(5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl methyl carbonate수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (70 μl; 0.5 mmol) and methyl chloroformate (39 μl; 0.5 mmol) were added to a solution of N-acetyl-colchicinol (0.178 g; 0.5 mmol) in THF (3 ml). The mixture was stirred at ambient temperature for 90 minutes. After removal of the insoluble material by filtration the residue was purified by flash chromatography eluting with dichloromethane/ethanol (98/2) to give (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl methyl carbonate.

후처리

  1. customAfter removal of the insoluble material
  2. filtrationby filtration the residue
  3. customwas purified by flash chromatography
  4. washeluting with dichloromethane/ethanol (98/2)

출처 및 근거

ORD 기록
ord-3c29999c92e14e74829436e9ffd7b469
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135502B1

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