Guanidine → HCID 178451196, compound

HRID 431501Notes

Reaction equation

HRID 431501 reaction equation
[C:1]([O:5][C:6](=[O:34])[C@@H:7]([NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19]([O:21]C)=O)=[CH:15][CH:16]=1)=[O:11])([CH3:4])([CH3:3])[CH3:2].[NH2:35][C:36]([NH2:38])=[NH:37]>O1CCCC1>[C:1]([O:5][C:6](=[O:34])[C@@H:7]([NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19](=[O:21])[NH:37][C:36]([NH2:38])=[NH:35])=[CH:15][CH:16]=1)=[O:11])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 3520GuanidineHCID 11005481HCID 11005481, compound

Product 1

HCID 178451196HCID 178451196, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.272 g (0.55 mmol) of the product obtained in step c) were suspended in 30 ml of dry tetrahydrofuran. 0.168 g (2.75 mmol) of guanidine (free base) were added. The resulting suspension was heated under reflux for 2.5 hours. The solvents were removed in vacuo and the residue was dissolved in 200 ml dichloromethane. The resulting solution was washed four times with 30 ml each of water. The organic phase was then dried with dry magnesium sulfate, filtered off and evaporated. 30 mg of a resinous material were obtained which was sufficiently pure for use in the subsequent step.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureunder reflux for 2.5 hours
  3. customThe solvents were removed in vacuo
  4. dissolutionthe residue was dissolved in 200 ml dichloromethane
  5. washThe resulting solution was washed four times with 30 ml each of water
  6. dry with materialThe organic phase was then dried with dry magnesium sulfate
  7. filtrationfiltered off
  8. customevaporated

Sources & evidence

ORD record
ord-945b670c0fc64f63969dad503bd6890e
Source dataset
uspto-grants-2003_12
Patent number
US06660728B2

Reaction notes

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