Di-tert-butyl dicarbonate → HCID 131720448, compound

HRID 727719Notes

Reaction equation

HRID 727719 reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[C:6]([N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)(=[NH:8])[NH2:7].[C:15]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)(=[NH:17])[NH2:16].[C:24](O[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>O1CCCC1.O>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[C:6]([N:9]1[CH2:14][CH2:13][N:12]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:11][CH2:10]1)(=[NH:7])[NH2:8].[C:15]([N:18]1[CH2:23][CH2:22][N:21]([C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[CH2:20][CH2:19]1)(=[NH:16])[NH2:17]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 44890711Sulfuric acid--piperazine-1-carboximidamide (1/2)

Product 1

HCID 131720448HCID 131720448, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2.50 g of 1-amidinopiperazine hemisulfate were dissolved in 60 ml of a 1:1 by volume mixture of tetrahydrofuran and water, and a solution of 3.40 g of di-t-butyl dicarbonate in 10 ml of tetrahydrofuran was added to the resulting solution, after which the mixture was stirred at room temperature for 2.5 hours. At the end of this time, the tetrahydrofuran was removed from the reaction mixture by distillation under reduced pressure, the insolubles were filtered off and the filtrate was evaporated to dryness under reduced pressure. The resulting residue was extracted with ethanol (twice, each time with 50 ml). and methanol (twice, each time with 50 ml). The extract was evaporated to dryness to obtain 2.48 g of the title compound, as crystals, melting at 278° C. (with decomposition).

Workup

  1. customAt the end of this time, the tetrahydrofuran was removed from the reaction mixture by distillation under reduced pressure
  2. filtrationthe insolubles were filtered off
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. extractionThe resulting residue was extracted with ethanol (twice, each time with 50 ml)
  5. customThe extract was evaporated to dryness

Sources & evidence

ORD record
ord-7c07c59303bc405e8ece3862fa604c97
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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