Acetic Acid → 3-(4-{[6-({(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}butyl)benzenesulfonamide acetate

HRID 2118164Notes

Reaction equation

HRID 2118164 reaction equation
[CH3:1][C:2]1(C)[O:7]C2C=CC([C@@H](O)CNCCCCCCOCCCCC3C=C(S(N)(=O)=O)C=CC=3)=CC=2C[O:3]1.C(O)(=O)C.[OH:42][C@H:43]([C:67]1[CH:72]=[CH:71][C:70]([OH:73])=[C:69]([CH2:74][OH:75])[CH:68]=1)[CH2:44][NH:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52][CH2:53][CH2:54][CH2:55][CH2:56][C:57]1[CH:58]=[C:59]([S:63]([NH2:66])(=[O:65])=[O:64])[CH:60]=[CH:61][CH:62]=1.C(O)(=O)C>O>[C:2]([OH:7])(=[O:3])[CH3:1].[OH:42][C@H:43]([C:67]1[CH:72]=[CH:71][C:70]([OH:73])=[C:69]([CH2:74][OH:75])[CH:68]=1)[CH2:44][NH:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52][CH2:53][CH2:54][CH2:55][CH2:56][C:57]1[CH:58]=[C:59]([S:63]([NH2:66])(=[O:65])=[O:64])[CH:60]=[CH:61][CH:62]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 866096623-(4-{[6-({(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}butyl)benzenesulfonamide acetate 3-{4-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}benzenesulfonamide

Product 1

HCID 426258193-(4-{[6-({(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}butyl)benzenesulfonamide acetateYield 220.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(4-{[6-({(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}butyl)benzenesulfonamide acetate 3-{4-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}benzenesulfonamide (0.283 g) was stirred with acetic acid (8 ml) and water (4 ml) at 70° for 35 min before evaporating to dryness. The residue was re-evaporated twice with toluene to give the title compound (0.318 g) LCMS RT=2.34 min ES+ve 495 (MH)+.

Workup

  1. custombefore evaporating to dryness
  2. customThe residue was re-evaporated twice with toluene

Sources & evidence

ORD record
ord-667931af867d4ba39f58355539787aa1
Source dataset
uspto-grants-2008_10
Patent number
US07442836B2

Reaction notes

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