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

HRID 720937

反応式

HRID 720937 の反応式
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

参加物

5

反応物 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 97865N-Acetylcolchicinol

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3c29999c92e14e74829436e9ffd7b469
出典データセット
uspto-grants-2006_11
特許番号
US07135502B1

関連ノート

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