Hydrochloric Acid → (S)-4-carboxy-4-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluoro-N-methylphenylsulfonamido)-N,N,N-trimethylbutan-1-aminium chloride

HRID 83838Notes

Reaction equation

HRID 83838 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][C:28]([S:32]([N:35]([C@@H:37]([CH2:41][CH2:42][CH2:43][N+:44]([CH3:47])([CH3:46])[CH3:45])[C:38]([O-:40])=[O:39])[CH3:36])(=[O:34])=[O:33])=[CH:27][C:26]=3[F:48])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:49][CH3:50].Cl>O>[Cl-:1].[C:38]([C@@H:37]([N:35]([CH3:36])[S:32]([C:28]1[CH:27]=[C:26]([F:48])[C:25]([CH2:24][S:23][C:14]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:49][CH3:50])[CH:4]=3)([CH3:10])[CH3:9])=[CH:12][N:13]=2)=[C:30]([F:31])[CH:29]=1)(=[O:34])=[O:33])[CH2:41][CH2:42][CH2:43][N+:44]([CH3:46])([CH3:47])[CH3:45])([OH:40])=[O:39]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86702237(S)-2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluoro-N-methylphenylsulfonamido)-5-(trimethylammonio)-pentanoate

Product 1

HCID 86702235(S)-4-carboxy-4-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluoro-N-methylphenylsulfonamido)-N,N,N-trimethylbutan-1-aminium chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (S)-2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluoro-N-methylphenylsulfonamido)-5-(trimethylammonio)-pentanoate in water was treated with 1N HCl (1.0 eq) and lyophilized to yield the title compound in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ 13.14 (s, 1H), 7.55 (d, J=6.7 Hz, 2H), 7.29 (s, 1H), 7.26 (d, J=8.3 Hz, 1H), 7.05-6.96 (m, 2H), 6.68-6.60 (m, 1H), 6.60-6.53 (m, 2H), 6.50 (dd, J=8.3, 2.0 Hz, 1H), 4.53 (dd, J=9.5, 4.7 Hz, 1H), 4.05 (s, 2H), 3.69 (s, 3H), 3.39-3.27 (m, 2H), 3.04 (s, 9H), 2.80 (s, 3H), 1.91-1.60 (m, 4H), 1.48 (s, 3H), 1.47 (s, 3H); 19F NMR (376 MHz, DMSO) δ −111.37-111.46 (m, 2F), −112.02-112.11 (m, 1F); MS (EI) m/z 753 (M+).

Sources & evidence

ORD record
ord-c8764c25bb204e959b97f37855c3b3b3
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

Loading…