Dicyclohexylcarbodiimide → (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl 3-[(2-tertbutoxycarbonylaminoacetyl)amino]propanoate

HRID 720936

反応式

HRID 720936 の反応式
[CH3:1][C:2]([NH:4][CH:5]1[C:15]2[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]=2[C:13]2[C:8](=[CH:9][C:10]([O:25][CH3:26])=[C:11]([O:23][CH3:24])[C:12]=2[O:21][CH3:22])[CH2:7][CH2:6]1)=[O:3].C1CCC(N=C=NC2CCCCC2)CC1.[C:42]([O:46][C:47]([NH:49][CH2:50][C:51]([NH:53][CH2:54][CH2:55][C:56](O)=[O:57])=[O:52])=[O:48])([CH3:45])([CH3:44])[CH3:43]>CN(C1C=CN=CC=1)C.ClCCl>[C:42]([O:46][C:47]([NH:49][CH2:50][C:51]([NH:53][CH2:54][CH2:55][C:56]([O:20][C:17]1[CH:18]=[CH:19][C:14]2[C:13]3[C:12]([O:21][CH3:22])=[C:11]([O:23][CH3:24])[C:10]([O:25][CH3:26])=[CH:9][C:8]=3[CH2:7][CH2:6][C@H:5]([NH:4][C:2](=[O:3])[CH3:1])[C:15]=2[CH:16]=1)=[O:57])=[O:52])=[O:48])([CH3:45])([CH3:44])[CH3:43]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 97865N-AcetylcolchicinolHCID 218938843-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)propanoic acid

生成物 1

HCID 69586968(5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl 3-[(2-tertbutoxycarbonylaminoacetyl)amino]propanoate収率 61%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of N-acetyl-colchicinol (0.357 g; 1 mmol), DCCI (0.248 g; 1.2 mmol), DMAP (0.025 g; 0.2 mmol) and (7) (0.246 g; 1 mmol) in dichloromethane (7 ml) was stirred under argon atmosphere for 5 hours. After removal of the insoluble material by filtration the residue was purified by flash chromatography eluting with dichloromethane/ethanol (92/8) to give (4) as a foam.

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 (92/8)

出典と根拠

ORDレコード
ord-efb6252309a44addb99e4cf18d2c0787
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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