HCID 69391369, compound → HCID 69387222, compound

HRID 916819Notes

Reaction equation

HRID 916819 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][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:47]=[CH:46][C:39]4[O:40]C(C)(C)[O:42][CH2:43][C:38]=4[CH:37]=3)[OH:35])=[CH:26][CH:25]=2)[CH:14]=1)[S:9]([NH2:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.O>[CH:6]([OH:7])=[O:5].[OH:35][C@H:34]([C:36]1[CH:47]=[CH:46][C:39]([OH:40])=[C:38]([CH2:43][OH:42])[CH:37]=1)[CH2:33][NH:32][CH2:31][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH2:22][CH2:21][O:20][CH2:19][C:15]2[CH:14]=[C:13]([NH:8][S:9]([NH2:12])(=[O:10])=[O:11])[CH:18]=[CH:17][CH:16]=2)=[CH:25][CH:26]=1.[CH:6]([OH:7])=[O:5].[C:1]([O:5][C:6]([N:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][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]([OH:35])[C:36]3[CH:47]=[CH:46][C:39]([OH:40])=[C:38]([CH2:43][OH:42])[CH:37]=3)=[CH:26][CH:25]=2)[CH:14]=1)[S:9]([NH2:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 69391369HCID 69391369, compound

Product 2

HCID 69387222HCID 69387222, compoundHCID 69405869HCID 69405869, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

N-(tert-Butoxycarbonyl)-N-[3-({2-[4-(2-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}ethyl)phenoxy]ethoxy}methyl)phenyl]sulfamide (15 mg) in acetic acid (1.5 ml) and water (0.5 ml) was heated at 75° C. for 0.5 h. The solution was then concentrated in vacuo and azeotroped with MeOH. The residue was purified by HPLC to give the title compounds N-{3-[(2-{4-[2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)ethyl]phenoxy}ethoxy)methyl]phenyl}sulfamide formate (1.5 mg) LCMS RT=2.21 min, ES+ve 532 (MH)+and N-(tert-butoxycarbonyl)-N-{3-[(2-{4-[2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)ethyl]phenoxy}ethoxy)methyl]phenyl}sulfamide formate (0.9 mg). LCMS RT=2.51 min ES+ve 630 (MH)+

Workup

  1. concentrationThe solution was then concentrated in vacuo
  2. customazeotroped with MeOH
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-1a5876815d854db096666edb379bd9c3
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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