N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide → N-(5-Benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-3-methyl-benzenesulfonamide

HRID 1846875Notes

Reaction equation

HRID 1846875 reaction equation
O[C:2]1C(=O)C=C(CNS(C2C=CC(C)=CC=2)(=O)=O)OC=1CO.[CH2:23]([O:30][C:31]1[C:32](=[O:50])[CH:33]=[C:34]([CH2:39][NH:40][S:41]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)(=[O:43])=[O:42])[O:35][C:36]=1[CH2:37][OH:38])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([O:30][C:31]1[C:32](=[O:50])[CH:33]=[C:34]([CH2:39][NH:40][S:41]([C:44]2[CH:45]=[CH:46][CH:47]=[C:48]([CH3:2])[CH:49]=2)(=[O:43])=[O:42])[O:35][C:36]=1[CH2:37][OH:38])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 86725693N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamideHCID 86725732N-(5-Hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-4-methyl-benzenesulfonamide

Product 1

HCID 86725717N-(5-Benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-3-methyl-benzenesulfonamideYield 41.35%

Procedure

N-(5-Benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-3-methyl-benzenesulfonamide (10-06) (3.7 g, 41.35%) was synthesized as a white solid from N-(5-hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-4-methyl-benzenesulfonamide (9-06) (7.0 g, 21.54 mmol) following the procedure described for N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide (10-01).

Sources & evidence

ORD record
ord-03882f86fcbd44b686f6edfce2a5e3e5
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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