Trifluoroacetic acid → HCID 178512543, compound

HRID 1497560Notes

Reaction equation

HRID 1497560 reaction equation
C(OC([NH:8][C:9](=[N:64]C(OC(C)(C)C)=O)[NH:10][C:11]1[CH:63]=[CH:62][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH:27][C@H:28]([C:54]([O:56]C(C)(C)C)=[O:55])[CH2:29][C:30]3[N:34]=[CH:33][N:32](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:31]=3)=[O:26])=[C:20]([Cl:61])[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:63]=[CH:62][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH:27][C@H:28]([C:54]([OH:56])=[O:55])[CH2:29][C:30]3[N:34]=[CH:33][NH:32][CH:31]=3)=[O:26])=[C:20]([Cl:61])[CH:19]=2)=[O:16])=[CH:13][CH:12]=1)[C:9]([NH2:64])=[NH:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454293HCID 178454293, compound

Product 1

HCID 178512543HCID 178512543, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-{[4-({4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoyl}oxy)-2-chlorophenyl]acetyl}-1-trityl-L-histidinate (265 mg) in dichloromethane (2.70 mL) was added trifluoroacetic acid (0.619 mL) under ice-cooling, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure and washed with water, and the filtrate was concentrated under reduced pressure. The residue was purified by ODS silica gel column chromatography (0.01 M hydrochloric acid-acetonitrile), and the purified product was dried under reduced pressure to obtain N-({4-[(4-carbamimidamidobenzoyl)oxy]-2-chlorophenyl}acetyl)-L-histidine 2 hydrochloride (54.1 mg).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washwashed with water
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by ODS silica gel column chromatography (0.01 M hydrochloric acid-acetonitrile)
  6. customthe purified product was dried under reduced pressure

Sources & evidence

ORD record
ord-aa0a335403174a0a9045221ee20a5861
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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