Trifluoroacetic acid → HCID 178460229, compound

HRID 1497562Notes

Reaction equation

HRID 1497562 reaction equation
C(OC([NH:8][C:9](=[N:54]C(OC(C)(C)C)=O)[NH:10][C:11]1[CH:53]=[CH:52][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:50])[C:25]([N:27]([CH2:36][C:37]3[CH:38]=[C:39]([CH:47]=[CH:48][CH:49]=3)[C:40]([O:42]C(C)(C)C)=[O:41])[CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])=[O:26])=[C:20]([Cl:51])[CH:19]=2)=[O:16])=[CH:13][CH:12]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:10]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:50])[C:25]([N:27]([CH2:36][C:37]3[CH:38]=[C:39]([CH:47]=[CH:48][CH:49]=3)[C:40]([OH:42])=[O:41])[CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[C:20]([Cl:51])[CH:19]=2)=[O:16])=[CH:52][CH:53]=1)[C:9]([NH2:54])=[NH:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178460230HCID 178460230, compound

Product 1

HCID 178460229HCID 178460229, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-{[{2-[4-({4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoyl}oxy)-2-chlorophenyl]propanoyl}(2-tert-butoxy-2-oxoethyl)amino]methyl}benzoate (180 mg) in dichloromethane (1.92 mL) was added trifluoroacetic acid (0.646 mL), followed by stirring at room temperature overnight. After completion, the reaction solution was concentrated under reduced pressure, and then to the residue was added acetonitrile (20.0 mL), followed by concentrating under reduced pressure again. This operation was repeated twice, to the residue was added a 50% aqueous acetonitrile solution (5.00 mL), and a 1 M aqueous sodium hydroxide solution (0.208 mL) was added thereto under ice-cooling. After stirring for 1 hour under ice-cooling, the precipitated crystals were collected by filtration, and washed with a 10% aqueous acetonitrile solution and then dried under reduced pressure to obtain 3-{[(2-{4-[(4-carbamimidamidobenzoyl)oxy]-2-chlorophenyl}propanoyl)(carboxymethyl)amino]methyl}benzoic acid (92 mg).

Workup

  1. concentrationAfter completion, the reaction solution was concentrated under reduced pressure
  2. additionto the residue was added acetonitrile (20.0 mL)
  3. concentrationby concentrating under reduced pressure again
  4. additionwas added a 50% aqueous acetonitrile solution (5.00 mL)
  5. additiona 1 M aqueous sodium hydroxide solution (0.208 mL) was added
  6. temperatureunder ice-cooling
  7. stirringAfter stirring for 1 hour under ice-
  8. temperaturecooling
  9. filtrationthe precipitated crystals were collected by filtration
  10. washwashed with a 10% aqueous acetonitrile solution
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-8489aeeda0ea403c909c06fdaf0f31fc
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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