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

HRID 262920

Reaction equation

HRID 262920 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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'-carbonyldimidazole. The solution is stirred overnight at room temperature and the solvents are evaporated to yield the title compound as a thick, orange oil.

Workup

  1. customthe protected amido-acid is precipitated from solution by addition of 150 ml, of water
  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

Sources & evidence

ORD record
ord-7823a943327146608f05ba76f41ca22c
Source dataset
uspto-grants-1979_05
Patent number
US04154756

Linked notes

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