4-Methoxybenzenesulfonyl chloride → 2-((1S)-1-{[(4-Methoxyphenyl)sulfonyl]amino}-7-oxooctyl)-5-phenyl-1H-imidazol-1-ium trifluoroacetate

HRID 251724Notes

Reaction equation

HRID 251724 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].FC(F)(F)C([O-])=O.C[NH+]1CCCC(C([NH:24][C@H:25]([C:34]2[NH2+:35][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:37][N:38]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]C(=O)C)=O)C1.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.[NH3+][C@H](C1[NH2+]C(C2C=CC=CC=2)=CN=1)CCCCCC(=O)C.CCN(CC)CC.[CH3:87][O:88][C:89]1[CH:94]=[CH:93][C:92]([S:95](Cl)(=[O:97])=[O:96])=[CH:91][CH:90]=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[CH3:87][O:88][C:89]1[CH:90]=[CH:91][C:92]([S:95]([NH:24][C@H:25]([C:34]2[NH2+:35][C:36]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:37][N:38]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:3](=[O:5])[CH3:2])(=[O:97])=[O:96])=[CH:93][CH:94]=1

Participants

6

Reactant 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 866279482-[(1S)-1-Ammonio-7-oxooctyl]-5-phenyl-1H-imidazol-1-ium bis(trifluoroacetate)HCID 873313811-methyl-3-({[(1S)-7-oxo-1-(5-phenyl-1h-imidazol-1-ium-2-yl)octyl]amino}carbonyl)piperidinium bis(trifluoroacetate)

Product 1

HCID 866279512-((1S)-1-{[(4-Methoxyphenyl)sulfonyl]amino}-7-oxooctyl)-5-phenyl-1H-imidazol-1-ium trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1, A3 and Et3N (1.1 eq.) in DCM was added 4-methoxybenzene sulfonyl chloride (1.1 eq.). The reaction mixture was stirred at RT for 3 hr and the mixture was washed with sat. aq. NaHCO3. The organic phase was concentrated under reduced pressure and the crude residue was purified by preparative RP-HPLC, using H2O (0.1% TFA) and MeCN (+0.1% TFA) as eluents (column: C18). The desired fractions were lyophilized to afford the titled compound B1 as a colourless oil. 1H NMR (300 MHz, CD3CN) δ: 8.87 (1H, d, J=9.3 Hz), 7.60-7.52 (4H, m), 7.51-7.40 (3H, m), 7.31 (1H, s), 6.79-6.63 (2H, m), 4.78-4.65 (1H, m), 3.51 (3H, s), 2.37 (2H, t, J=7.3 Hz), 2.04 (3H, s), 1.89-1.78 (2H, m), 1.51-1.32 (3H, m), 1.31-1.14 (3H, m). MS (ES) C24H29N3O4S requires: 455, found: 456 (M+H)+.

Workup

  1. washthe mixture was washed with sat. aq. NaHCO3
  2. concentrationThe organic phase was concentrated under reduced pressure
  3. customthe crude residue was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-fd412b20ec71417bb521c562e4407355
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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