Trifluoroacetic acid → HCID 22122237, compound

HRID 1417229Notes

Reaction equation

HRID 1417229 reaction equation
C(OC([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:41])[CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][N:28]([CH2:31][C:32]([O:34]C(C)(C)C)=[O:33])[C:27](=[O:39])[C:26]2=[O:40])=[CH:16][CH:15]=1)=[NH:13])=O)C1C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:12]([C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:41])[CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][N:28]([CH2:31][C:32]([OH:34])=[O:33])[C:27](=[O:39])[C:26]2=[O:40])=[CH:18][CH:19]=1)(=[NH:11])[NH2:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 140397802HCID 140397802, compound

Product 1

HCID 22122237HCID 22122237, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.28 g of tert-butyl [4-[4-(4-benzyloxycarbonylamidinophenylamino)-4-oxobutyl]-2,3-dioxopiperazin-1-yl]acetate in 2.8 ml of methylene chloride was added 1.4 ml of trifluoroacetic acid, and the resulting mixture was stirred at room temperature for 12 hours and then distilled under reduced pressure to remove the solvent. To the resulting residue were added 0.08 g of 5% palladium-carbon and 5.6 ml of N,N-dimethylformamide, followed by hydrogenation at ordinary temperature and atmospheric pressure for 3 hours. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. To the resulting concentrate were added 5 ml of water and 0.042 g of sodium hydrogencarbonate to obtain a homogeneous solution. This solution was purified by a reversed phase column chromatography (eluent: a 10% aqueous acetonitrile solution) to obtain 0.08 g of [4-[4-(4-amidinophenylamino)-4-oxobutyl]-2,3-dioxopiperazin-1yl]acetic acid as colorless crystals.

Workup

  1. distillationdistilled under reduced pressure
  2. customto remove the solvent
  3. additionTo the resulting residue were added 0.08 g of 5% palladium-carbon and 5.6 ml of N,N-dimethylformamide
  4. waitfollowed by hydrogenation at ordinary temperature and atmospheric pressure for 3 hours
  5. customAfter completion of the reaction
  6. filtrationthe catalyst was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. concentrationTo the resulting concentrate
  9. additionwere added 5 ml of water and 0.042 g of sodium hydrogencarbonate
  10. customto obtain a homogeneous solution
  11. customThis solution was purified by a reversed phase column chromatography (eluent

Sources & evidence

ORD record
ord-6239055fd88145e8a8ce9ce81f594db7
Source dataset
uspto-grants-1999_03
Patent number
US05877174

Reaction notes

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