HCID 178502575, compound → HCID 178502574, compound

HRID 376547Notes

Reaction equation

HRID 376547 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH:17][O:18][C:19]([O:21][CH3:22])=[O:20])=[NH:16])=[CH:10][CH:9]=1)=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]([NH:17][O:18][C:19]([O:21][CH3:22])=[O:20])=[NH:16])=[CH:12][CH:13]=1)([OH:7])=[O:5]

Participants

3

Reactant 1

HCID 178502575HCID 178502575, compound

Product 1

HCID 178502574HCID 178502574, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In 25 ml of trifluoroacetic acid was dissolved 9.2 g of N-(4-t-butoxycarbonylphenyl)-N'-methoxycarbonyloxyguanidine produced in Reference Example 31. The solution was stirred for two hours at room temperature. The reaction mixture was concentrated under reduced pressure, to which was added 100 ml of water. To the mixture was added sodium hydrogencarbonate to adjust the pH to 6. The resulting crystalline precipitate was collected by filtration, followed by recrystallization from tetrahydrofuranethyl acetate to afford 4.53 g of the title compound as a colorless crystalline product.

Workup

  1. customproduced in Reference Example 31
  2. concentrationThe reaction mixture was concentrated under reduced pressure, to which
  3. additionwas added 100 ml of water
  4. additionTo the mixture was added sodium hydrogencarbonate
  5. filtrationThe resulting crystalline precipitate was collected by filtration
  6. customfollowed by recrystallization from tetrahydrofuranethyl acetate

Sources & evidence

ORD record
ord-5718e04c6df34cbbb4b3bc2c573c57c7
Source dataset
uspto-grants-2000_02
Patent number
US06020334

Reaction notes

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