3-{4-[(6-{[2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}benzenesulfonamide → 3-{4-[(6-{[(2S)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}benzenesulfonamide

HRID 2117664Notes

Reaction equation

HRID 2117664 reaction equation
[CH3:1][C:2]1([CH3:37])[O:7][C:6]2[CH:8]=[CH:9][C:10]([CH:12]([OH:36])[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([S:32]([NH2:35])(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=3)=[CH:11][C:5]=2[CH2:4][O:3]1>C(O)C.CCCCCCC>[CH3:1][C:2]1([CH3:37])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]([OH:36])[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([S:32]([NH2:35])(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=3)=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

3

Reactant 1

HCID 218954733-{4-[(6-{[2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}benzenesulfonamide

Product 1

HCID 426255903-{4-[(6-{[(2S)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}benzenesulfonamideYield 23.8%

Reagents, catalysts & solvents 1

HCID 22502148Ethanol heptaneSolvent

Procedure

Resolution of 3-{4-[(6-{[2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}benzenesulfonamide (0.403 g) on an HPLC Chiralcel OJ column using 40% ethanol/heptane afforded the title compound (0.096 g).

Sources & evidence

ORD record
ord-7f91a72558cf44ef967a8ede33b2064b
Source dataset
uspto-grants-2008_10
Patent number
US07442719B2

Reaction notes

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