Trifluoroacetic acid → HCID 178513191, compound

HRID 749082Notes

Reaction equation

HRID 749082 reaction equation
[CH2:1]([S:8]([NH:11][C:12]1[C:13](=[O:43])[N:14]([CH2:18][C:19]([N:21]([CH2:29][CH2:30][O:31][NH:32][C:33]([NH2:42])=[N:34]C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[O:20])[CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47]>C(Cl)Cl>[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47].[CH2:1]([S:8]([NH:11][C:12]1[C:13](=[O:43])[N:14]([CH2:18][C:19]([NH:21][CH2:29][CH2:30][O:31][NH:32][C:33]([NH2:42])=[NH:34])=[O:20])[CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454315HCID 178454315, compound

Product 1

HCID 178513191HCID 178513191, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-benzylsulfonylamino-1-{[N,N′-di(tert-butoxycarbonyl)] [(2-guanidinooxyethyl)aminocarbonylmethyl]}-2-pyridinone (155 mg, 0.25 mmol), as prepared in the preceding step, and trifluoroacetic acid (2 mL) in methylene chloride (3 mL) was stirred at room temperature for 2 h. After evaporation of the solvent in vacuo, the residue was purified by Waters Sep-Pak (10 g, 10% methanol in methylene chloride) to give the title compound as a colorless foam (160 mg, 92%). 1H-NMR (300 MHz, DMSO c6) δ 11.00 (s, 1H), 8.66 (s, 1H), 8.45 (t, J=5.3 Hz, 1H), 7.72 (br s, 4H), 7.40 (d, J=6.9 Hz, 1H), 7.33 (m, 5H), 7.19 (d, J=7.0 Hz, 1H), 6.19 (d, J=7.0 Hz, 1H), 4.62 (s, 2H), 4.55 (s, 2H), 3.83 (t, J=5.1 Hz, 2H), 3.39 (m, 2H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C17H22N6O5S: 423.1 (M+H), 445.1 (M+Na); Found: 423.3, 445.0.

Workup

  1. customAfter evaporation of the solvent in vacuo
  2. customthe residue was purified by Waters Sep-Pak (10 g, 10% methanol in methylene chloride)

Sources & evidence

ORD record
ord-765225c601e94a6a94c9ae89256711fb
Source dataset
uspto-grants-2008_07
Patent number
US07402586B2

Reaction notes

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