NSC677645 → HCID 14987866, compound

HRID 2184616Notes

Reaction equation

HRID 2184616 reaction equation
[C:1]1([CH3:42])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH2:18][CH2:17][N:16]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:43][C:44]1([CH3:52])[O:51][CH2:50][CH:49]2[CH:47]([O:48]2)[CH2:46][O:45]1>CN(C)C=O>[OH:48][CH:49]1[CH2:50][O:51][C:44]([CH3:52])([CH3:43])[O:45][CH2:46][CH:47]1[N:13]1[CH2:14][CH2:15][N:16]([S:32]([C:35]2[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=2)(=[O:34])=[O:33])[CH2:17][CH2:18][N:19]([S:22]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)(=[O:24])=[O:23])[CH2:20][CH2:21][N:10]([S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:42])=[CH:6][CH:5]=2)(=[O:9])=[O:8])[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 386072NSC677645HCID 110947474,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

Product 1

HCID 14987866HCID 14987866, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 g (78.76 mmol) of 4,7,10-tris(p-toluenesulfonyl)-1,4,7,10-tetraazacyclododecane and 13.63 g (94.51 mmol) of 4,4-dimethyl-3,5,8-trioxabicyclo-[5.1.0]-octane are dissolved in 300 ml of dimethylformamide and heated in an autoclave for 24 hours to 170° C. It is evaporated to dryness and the residue is chromatographed on silica gel (mobile solvent: methylene chloride/hexane/acetone: 10/5/1). The main fractions are concentrated by evaporation and recrystallized from methyl tert-butyl ether/methanol. Yield: 52.76 g (86% of theory) of a cream-colored powder.

Workup

  1. temperatureheated in an autoclave for 24 hours to 170° C
  2. customIt is evaporated to dryness
  3. customthe residue is chromatographed on silica gel (mobile solvent: methylene chloride/hexane/acetone: 10/5/1)
  4. concentrationThe main fractions are concentrated by evaporation
  5. customrecrystallized from methyl tert-butyl ether/methanol

Sources & evidence

ORD record
ord-7cd2bc0ad13a41e18d9b474bcb5e46e9
Source dataset
uspto-grants-2002_06
Patent number
US06399043B1

Reaction notes

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