Pyridine → N-(t-butyloxycarbonyl)-4-(n-hexadecylamino)benzoyl-imidazole

HRID 1733519

반응식

HRID 1733519 반응식
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1)[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].O1CCOCC1.[C:33]([O:37][C:38]([N:40]=[N+]=[N-])=[O:39])([CH3:36])([CH3:35])[CH3:34].[N:43]1[CH:48]=CC=[CH:45][CH:44]=1>>[C:33]([O:37][C:38]([N:40]1[CH:45]=[CH:44][N:43]=[C:48]1[C:22](=[O:24])[C:21]1[CH:20]=[CH:19][C:18]([NH:17][CH2:1][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])=[CH:26][CH:25]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34]

참가 물질

5

반응물 4

HCID 1049PyridineHCID 312751,4-DioxaneHCID 472634-(Hexadecylamino)benzoic acidHCID 61256Carbonazidic acid, 1,1-dimethylethyl ester

생성물 1

HCID 20437338N-(t-butyloxycarbonyl)-4-(n-hexadecylamino)benzoyl-imidazole

실험 절차

A solution of 10 g. of 4-(n-hexadecylamino)benzoic acid in 100 ml. dioxane is treated with 4.0 g. of t-butylazidoformate and 10 ml. pyridine. After stirring at room temperature for 18 hours, the protected amido-acid is precipitated from solution by addition of 150 ml. of water. The product is collected and thoroughly dried. The crude product is dissolved in 200 ml. of a mixture consisting of methylene chloride/dimethoxy ethane/pyridine (1:4:1), and to this is added 5.4 g. of 1,1'-carbonyldiimidazoye. The solution is stirred overnight at room temperature and the solvents are evaporated to yield the title compound as a thick, orange oil.

후처리

  1. customthe protected amido-acid is precipitated from solution by addition of 150 ml
  2. customThe product is collected
  3. customthoroughly dried
  4. dissolutionThe crude product is dissolved in 200 ml
  5. additionto this is added 5.4 g
  6. stirringThe solution is stirred overnight at room temperature
  7. customthe solvents are evaporated

출처 및 근거

ORD 기록
ord-0a26e91cfc5142abbc24a6846979e2cf
출처 데이터셋
uspto-grants-1980_12
특허 번호
US04242273

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