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

HRID 1699651노트

반응식

HRID 1699651 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
4 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d0bb095d68224a32b5e1a8ef9aa21fd5
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06348451B1

반응 노트

불러오는 중…