p-Chlorobenzenesulfonic acid → HCID 131727139, compound

HRID 2118360Notes

Reaction equation

HRID 2118360 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:12]1([S:17]([C:20]2[CH:21]=[C:22]([CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][CH2:38][C@@H:39]([C:41]3[CH:46]=[CH:45][C:44]([OH:47])=[C:43]([CH2:48][OH:49])[CH:42]=3)[OH:40])[CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1>CC(O)C>[CH:12]1([S:17]([C:20]2[CH:21]=[C:22]([CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][CH2:38][C@@H:39]([C:41]3[CH:46]=[CH:45][C:44]([OH:47])=[C:43]([CH2:48][OH:49])[CH:42]=3)[OH:40])[CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O-:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7400p-Chlorobenzenesulfonic acidHCID 10076176HCID 10076176, compound

Product 1

HCID 131727139HCID 131727139, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chlorobenzene sulfonic acid (19 mg) was added to a solution of 4-{(1R)-2-[(6-{4-[3-(cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl)phenol (55 mg) (dissolved by gentle warming) in propan-2-ol (0.5 ml) at 21°. After a few minutes crystals had separated out. These were collected, and rinsed with propan-2-ol to give crystals of the title compound, δ (DMSO-d6) 9.40 (1H,s), 8.42 (2H, br s), 7.72-7.67 (2H, m), 7.62-7.55 (4H, m), 7.38 (2H, m), 7.32 (1H, d, J=2 Hz), 7.05 (1H, dd, J 2,8 Hz), 6.75 (1H, d, J=8 Hz), 5.97 (1H, br s), 5.00 (1H, v br s), 4.76 (1H, br d, J=9 Hz), 4.49 (2H, s), 3.75 (1H m), 3.32 (4H, partially obscured t), 3.10-2.87 (4H, 2m), 2.71 (2H, t, J=7 Hz), 1.90-1.25 (20H, m).

Workup

  1. customAfter a few minutes crystals had separated out
  2. customThese were collected
  3. washrinsed with propan-2-ol

Sources & evidence

ORD record
ord-899843818dfe4e57b89f7cee87c64937
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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