N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide → N-(5-Benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-4-chloro-benzenesulfonamide

HRID 1846884Notes

Reaction equation

HRID 1846884 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:29])[CH:11]=[C:12]([CH2:17][NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[O:13][C:14]=1[CH2:15][OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C(=O)C=C(CNS(C2C=CC=CC=2)(=O)=O)OC=1C=O)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]1[C:10](=[O:29])[CH:11]=[C:12]([CH2:17][NH:18][S:19]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)(=[O:21])=[O:20])[O:13][C:14]=1[CH:15]=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 86725694N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamideHCID 86725740N-(5-Benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-4-chloro-benzenesulfonamide

Product 1

HCID 86725741N-(5-Benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-4-chloro-benzenesulfonamideYield 85.3%

Procedure

N-(5-Benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-4-chloro-benzenesulfonamide (11-07) (3.4 g, 85.22%) was synthesized as a white solid from N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-4-chloro-benzenesulfonamide (10-07) (4.0 g, 9.19 mmol) following the procedure described for N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide (11-01).

Sources & evidence

ORD record
ord-c06597629d2e4339a16765633a881727
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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