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3-(Naphth-2-yl)acrylic acid → 3-(3-{[7-({(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)heptyl]oxy}propyl)benzenesulfonamide (E)-3-(napthalen-2-yl)-2-propenoate

HRID 720859
Notes
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Reaction equation

HRID 720859 reaction equation
[OH:1][C@H:2]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([CH2:33][OH:34])[CH:27]=1)[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[C:18]([S:22]([NH2:25])(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1.[CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][C:36]=1/[CH:45]=[CH:46]/[C:47]([OH:49])=[O:48]>C(O)C>[CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][C:36]=1/[CH:45]=[CH:46]/[C:47]([OH:49])=[O:48].[OH:1][C@H:2]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([CH2:33][OH:34])[CH:27]=1)[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[C:18]([S:22]([NH2:25])(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7358353-(Naphth-2-yl)acrylic acidHCID 102890653-(3-{[7-({(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)heptyl]oxy}propyl)benzenesulfonamide

Product 1

HCID 866096433-(3-{[7-({(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)heptyl]oxy}propyl)benzenesulfonamide (E)-3-(napthalen-2-yl)-2-propenoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(3-{[7-({(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)heptyl]oxy}propyl)benzenesulfonamide (1 g) was taken up in ethanol (6 ml) at room temperature with stirring and (E)-3-(napthalen-2-yl)-2-propenoic acid (0.39 g) added. The mixture was heated to ca 60° C. until a solution formed. The solution was cooled to room temperature and seed crystals of the title compound added. The mixture was aged for 65 h, the product filtered, washed with ethanol (1 ml) and dried to give the title compound (1.05 g) M Pt.=135° C.–146° C.

Workup

  1. temperatureThe mixture was heated to ca 60° C. until a solution
  2. customformed

Sources & evidence

ORD record
ord-080f25d6a676454191103d410294c293
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07135600B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes