N,N-Diethylaniline → (R)-2-Amino-9-(2-stearoyloxymethyl-4-(N-tert-butoxycarbonyl-L-valyloxy)butyl)-6-chloropurine

HRID 48556

반응식

HRID 48556 반응식
[C:1]([O:20][CH2:21][C@H:22]([CH2:35][CH2:36][O:37][C:38](=[O:51])[C@H:39]([CH:48]([CH3:50])[CH3:49])[NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:23][N:24]1[CH:32]=[N:31][C:30]2[C:29](=O)[NH:28][C:27]([NH2:34])=[N:26][C:25]1=2)(=[O:19])[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][CH2:16][CH2:17][CH3:18].C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:65])=O>C(#N)C.[Cl-].C[N+](C)(C)C>[NH2:34][C:27]1[N:26]=[C:25]2[C:30]([N:31]=[CH:32][N:24]2[CH2:23][C@H:22]([CH2:21][O:20][C:1](=[O:19])[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][CH2:16][CH2:17][CH3:18])[CH2:35][CH2:36][O:37][C:38](=[O:51])[C@H:39]([CH:48]([CH3:50])[CH3:49])[NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[C:29]([Cl:65])[N:28]=1

참가 물질

6

반응물 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 135796494(R)-9-(2-stearoyloxymethyl-4-(N-tert-butoxycarbonyl-L-valyloxy)butyl)guanine

생성물 1

HCID 53751265(R)-2-Amino-9-(2-stearoyloxymethyl-4-(N-tert-butoxycarbonyl-L-valyloxy)butyl)-6-chloropurine

시약·촉매·용매 2

HCID 6379Tetramethylammonium chloride촉매HCID 6342Acetonitrile용매

실험 절차

To a solution of (R)-9-(2-stearoyloxymethyl-4-(N-tert-butoxycarbonyl-L-valyloxy)butyl)guanine from step 2 of Example 1 (646 mg, 0.9 mmole) in acetonitrile were added tetramethylammonium chloride (427 mg, 2.7 mmole), N,N-diethylaniline (0.716 ml, 4.5 mmole) and phosphorous oxychloride (0.417 ml, 4.5 mmole). The reaction was kept under reflux and the progression monitored by TLC. After 3 hours the reaction mixture was evaporated in vacuo and the residue was dissolved in dichloromethane, then poured into cold sodium hydrogen carbonate aqueous solution. The organic phase was evaporated and purified by silica gel column chromatography. Yield: 251 mg.

후처리

  1. temperatureunder reflux
  2. customAfter 3 hours the reaction mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane
  4. additionpoured into cold sodium hydrogen carbonate aqueous solution
  5. customThe organic phase was evaporated
  6. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f89c35cd0b20477090c85eea32b0ce0d
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703394B2

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