Hydroxyamine hydrochloride → HCID 54254517, compound

HRID 2270352Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]([CH2:20][C:21]#[C:22][CH3:23])([CH2:16][C:17]#[C:18][CH3:19])[C:13](O)=[O:14])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[NH2:25][OH:26]>>[OH:26][NH:25][C:13](=[O:14])[C:12]([S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])([CH2:20][C:21]#[C:22][CH3:23])[CH2:16][C:17]#[C:18][CH3:19]

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 18416736HCID 18416736, compound

Product 1

HCID 54254517HCID 54254517, compoundYield 89%

Procedure

2-(4-Methoxy-benzenesulfonyl)-2-but-2-ynyl-hex-4-ynoic acid hydroxyamide was prepared according to the method as outlined in example 1. Starting from 2-(4-methoxy-benzenesulfonyl)-2-but-2-ynyl-hex-4-ynoic acid (0.27 g, 0.81 mmol) and hydroxylamine hydrochloride (0.70 g, 10 mmol), 0.23 g of the product was isolated. Yield 89%; white solid; mp 135-137° C.; MS: 349.9 (M+H)+1 ; 1H NMR (300 MHz, DMSO-d6) δ1.67 (s, 6H), 2.70-3.10 (m, 4H), 3.88 (s, 3H), 7.15 (d, J=10.0 Hz, 2H), 7.71 (d, J=10.0 Hz, 2H), 9.20 (brs, 1H), 10.90 (brs, 1H); IR (KBr, cm−1): 3301s, 3161m, 2922m, 1640m, 1595s, 1500m.

Sources & evidence

ORD record: ord-fb2a7acb291a41d49907a79361c4aada
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331563B1

Reaction notes

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