Hydroxyamine hydrochloride → HCID 54435302, compound

HRID 991077Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]([CH2:19][C:20]#[C:21][CH3:22])([CH2:15][C:16]#[C:17][CH3:18])[C:12](O)=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[NH2:24][OH:25]>>[OH:25][NH:24][C:12](=[O:13])[C:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])([CH2:19][C:20]#[C:21][CH3:22])[CH2:15][C:16]#[C:17][CH3:18]

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 22713323HCID 22713323, compound

Product 1

HCID 54435302HCID 54435302, compoundYield 77%

Procedure

2-(4-Fluoro-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-fluoro-benzenesulfonyl)-2-but-2-ynyl-hex-4-ynoic acid (0.26 g, 0.81 mmol) and hydroxylamine hydrochloride (0.70 g, 10 mmol), 0.21 g of the product was isolated. Yield 77%; white solid; mp 161-163° C.; MS:338.1(M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.67 (s, 6H), 2.80-3.10 (m, 4H), 7.51 (dd, J=9.0, 9.0 Hz, 2H), 7.87 (m, 2H), 9.26 (brs, 1H), 10.95 (brs, 1H); IR (KBr, cm-1): 3336 s, 3245 m, 1681 s, 1589 m, 1493 m; Anal. Calc'd for C16H16FNO4S: C, 56.96; H, 4.78; N, 4.15. Found: C, 56.59; H, 4.75; N, 4.04.

Sources & evidence

ORD record: ord-e7d345c6771e4dcdbf0ff0b0e5a48794
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06462073B2

Reaction notes

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