Dicyclohexylcarbodiimide → N-lysyl-5'-O-palmitoyl-deoxycytidine

HRID 381236ノート

反応式

HRID 381236 の反応式
[C:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[CH:31][C:29]([NH2:30])=[N:28][C:26]2=[O:27])[CH2:22][C@@H:21]1[OH:33])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(OC([N:41](C(OC(C)(C)C)=O)[C@H:42]([C:48](O)=[O:49])[CH2:43][CH2:44][CH2:45][CH2:46][NH2:47])=O)(C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1>CC(N(C)C)=O>[NH2:41][C@H:42]([C:48]([NH:30][C:29]1[CH:31]=[CH:32][N:25]([C@@H:23]2[O:24][C@H:20]([CH2:19][O:18][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C@@H:21]([OH:33])[CH2:22]2)[C:26](=[O:27])[N:28]=1)=[O:49])[CH2:43][CH2:44][CH2:45][CH2:46][NH2:47]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 154843895'-O-palmitoyldeoxycytidineHCID 22792075Di-tert-butoxycarbonyl-lysine

生成物 1

HCID 15484390N-lysyl-5'-O-palmitoyl-deoxycytidine

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
4 °C

実験手順

14 grams of 5′-O-palmitoyl-deoxycytidine is dissolved in 100 ml dimethylacetamide, 1 molar equivalent of di-tert-butoxycarbonyl-lysine is added, and the mixture is cooled in an ice bath. 1.2 molar equivalents (7.4 g) of dicyclohexylcarbodiimide are added and the mixture is stirred at 4° C. for 90 hours. The precipitate dicyclohexylurea) is removed by filtration. 100 ml of water is added to the filtrate, followed by 1 liter of ethyl acetate. N4-(di-N-tert-butoxycarbonyl-lysyl)-5′-O-palmitoyl-deoxycytidine is separated from unreacted reagents by chromatography over silica gel. The t-butoxycarbonyl protecting groups are removed by the standard methods of treatment with an acid, such as trifluoroacetic acid.

後処理

  1. temperaturethe mixture is cooled in an ice bath
  2. customThe precipitate dicyclohexylurea) is removed by filtration
  3. addition100 ml of water is added to the filtrate
  4. customN4-(di-N-tert-butoxycarbonyl-lysyl)-5′-O-palmitoyl-deoxycytidine is separated from unreacted reagents by chromatography over silica gel
  5. customThe t-butoxycarbonyl protecting groups are removed by the standard methods of treatment with an acid, such as trifluoroacetic acid

出典と根拠

ORDレコード
ord-f419e2a42a7c4d00b6d4f77523be8f21
出典データセット
uspto-grants-2001_10
特許番号
US06306834B1

反応ノート

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