Hydroxyamine hydrochloride → HCID 10274434, compound

HRID 1251420Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]([CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)([CH2:15][C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:12](O)=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[NH2:31][OH:32]>>[OH:32][NH:31][C:12](=[O:13])[C:11]([S:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)(=[O:9])=[O:10])([CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH2:15][C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 18416789HCID 18416789, compound

Product 1

HCID 10274434HCID 10274434, compoundYield 29%

Procedure

2-(4-Fluoro-benzenesulfonyl)-2-pyridin-3-ylmethyl-dec-4-ynoic acid hydroxyamide was prepared according to the method as outlined in Example 1. Starting from 2-(4-fluoro-benzenesulfonyl)-2-pyridin-3-ylmethyl-dec-4-ynoic acid (0.67 g, 1.62 mmol) and hydroxylamine hydrochloride (1.39 g, 20 mmol), 0.22 g of the product was isolated. Yield 29%; white solid, mp 180-182° C., MS: 433.2 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ0.84 (t, J=6.8 Hz, 3H), 1.20-1.40 (m, 6H), 1.90-2.05 (m, 2H), 2.75 (d, J=19.9 Hz, 1H), 2.94 (d, J=19.9 Hz, 1H), 3.54 (d, J=13.7 Hz, 1H), 3.75 (d, J=13.7 Hz, 1H), 7.40-7.60(m, 2H), 7.70-8.00 (m, 3H), 8.30-8.40 (m, 1H), 8.70-8.80 (m, 2H), 11.1 (brs, 1H); IR (KBr, cm−1): 3154m, 3105s, 3067m, 2957s, 2933s, 2873m, 1690s, 1631m Anal. Calc'd for C22H25FN2O4S.HCl: C, 56.34; H, 5.59; N, 5.97. Found.: C, 56.18; H, 5.54; N,5.76.

Sources & evidence

ORD record: ord-3dfba63a7b444d25a5bb75e4ab9a5931
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06342508B1

Reaction notes

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