Benzoyl chloride → HCID 16760627, compound

HRID 2371426Notes

Reaction equation

HRID 2371426 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C@:11]12[N:27]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=4[C:34]4[C:35]5[CH2:40][NH:39][C:37](=[O:38])[C:36]=5[C:24]5=[C:25]([C:26]=43)[N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=35)[C@H:15]([O:16]1)[CH2:14][C@@H:13]([NH:41][CH3:42])[C@H:12]2[O:43][CH3:44].C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[CH3:10][C:11]12[N:27]3[C:26]4=[C:25]5[N:17]([C:18]6[C:23]([C:24]5=[C:36]5[C:37](=[O:38])[NH:39][CH2:40][C:35]5=[C:34]4[C:33]4[C:28]3=[CH:29][CH:30]=[CH:31][CH:32]=4)=[CH:22][CH:21]=[CH:20][CH:19]=6)[CH:15]([O:16]1)[CH2:14][CH:13]([N:41]([C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8])[CH3:42])[CH:12]2[O:43][CH3:44]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 44259StaurosporineHCID 81531Diisopropylethylamine

Product 1

HCID 16760627HCID 16760627, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

0.035 ml (0.3 mmol) of benzoyl chloride is added at room temperature to a solution of 116.5 mg (0.25 mmol) of staurosporine and 0.065 ml (0.38 mmol) of N,N-diisopropylethylamine in 2 ml of chloroform and the whole is stirred for 10 minutes. The reaction mixture is diluted with chloroform, washed with sodium bicarbonate solution, dried over magnesium sulphate and concentrated by evaporation. The crude product is chromatographed on silica gel (eluant:methylene chloride/ethanol 30:1); m.p. 235°-247° with colour turning brown.

Workup

  1. washwashed with sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated by evaporation
  4. customThe crude product is chromatographed on silica gel (eluant:methylene chloride/ethanol 30:1)

Sources & evidence

ORD record
ord-af109c03220e4f98b428d2d5f58c4fe2
Source dataset
uspto-grants-1992_03
Patent number
US05093330

Reaction notes

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