Succinic Acid → n-{5-[(1r)-2-({2-[4-(2-{3-[(1r)-3-(Diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide succinate salt

HRID 1433308Notes

Reaction equation

HRID 1433308 reaction equation
[CH:1]([N:4]([CH:48]([CH3:50])[CH3:49])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH:32][CH2:33][C@@H:34]([C:36]3[CH:37]=[CH:38][C:39]([OH:47])=[C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH:41]=3)[OH:35])=[CH:26][CH:25]=2)[CH:17]=[CH:18][C:19]=1[OH:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[C:51]([OH:58])(=[O:57])[CH2:52][CH2:53][C:54]([OH:56])=[O:55]>CO.O>[C:51]([OH:58])(=[O:57])[CH2:52][CH2:53][C:54]([OH:56])=[O:55].[CH:48]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH:32][CH2:33][C@@H:34]([C:36]3[CH:37]=[CH:38][C:39]([OH:47])=[C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH:41]=3)[OH:35])=[CH:26][CH:25]=2)[CH:17]=[CH:18][C:19]=1[OH:20])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:50])[CH3:49]

Participants

5

Reactant 2

HCID 1110Succinic AcidHCID 57933169N-{5-[(1R)-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide

Product 1

HCID 68928990n-{5-[(1r)-2-({2-[4-(2-{3-[(1r)-3-(Diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide succinate salt

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

N-{5-[(1R)-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide (Example 5, 2000 mg, 2.84 mmol) was dissolved in methanol (8 ml) and succinic acid (336 mg, 2.84 mmol) in water (2 ml) and methanol (2 ml) was added in one portion to the stirred solution at room temperature. Further water was added until the salt appeared as a gum which was seeded with a small crystal of the salt previously isolated. The mixture was left overnight and stirred occasionally to aid crystallisation. After 5 days the solid was filtered and dried in vacuo to furnish the title compound as a white crystalline solid, 2336 mg, m.p. 148-150° C.

Workup

  1. custompreviously isolated
  2. customcrystallisation
  3. filtrationAfter 5 days the solid was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-65ec2149093841d7b2d5e3bf1bcd7952
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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