Di-tert-butyl dicarbonate → HCID 131720448, compound

HRID 362100Notes

Reaction equation

HRID 362100 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) and methanol (twice, each time with 50 ml)
  5. customThe extract was evaporated to dryness

Sources & evidence

ORD record
ord-8b36d9d69fc04edc9cd3069cc7c43e60
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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