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 2117686Notes

Reaction equation

HRID 2117686 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

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. δ (MeOH-d4) 7.95 (1H, s), 7.87 (3H, m), 7.75 (3H, m), 7.60 (1H, d, J 16 Hz), 7.45 (5H, m), 7.40 (1H, m), 6.8 (1H, d, J 8 Hz), 6.65 (1H, d, J 16 Hz), 4.9 (1H, m), 4.65 (2H, s), 3.4 (4H, m), 3.12 (2H, m), 3.05 (2H, br t, J 8 Hz), 2.75 (2H, t, J 8 Hz), 1.87 (2H, m), 1.72 (2H, m), 1.56 (2H, m), 1.40 (6H, m).

Workup

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

Sources & evidence

ORD record
ord-6186e002601a40c8b837cf3338c88dca
Source dataset
uspto-grants-2008_10
Patent number
US07442719B2

Reaction notes

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