Potassium Bromide → HCID 54415059, compound

HRID 2270350Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]([CH2:24][C:25]#[C:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH2:16][C:17]#[C:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:13](O)=[O:14])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[NH2:33][OH:34].[K+].[Br-]>>[OH:34][NH:33][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])([CH2:24][C:25]#[C:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:16][C:17]#[C:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Reactant 3

HCID 253877Potassium Bromide

HCID 443297Hydroxyamine hydrochloride

HCID 18416727HCID 18416727, compound

Product 1

HCID 54415059HCID 54415059, compoundYield 62%

Procedure

2-(4-Methoxy-benzenesulfonyl)-2-oct-2-ynyl-dec4-ynoic acid hydroxyamide was prepared according to the method as outlined in example 1. Starting from 2-(4-methoxy-benzenesulfonyl)-2-oct-2-ynyl-dec-4-ynoic acid (0.36 g, 0.81 mmol) and hydroxylamine hydrochloride (0.70 g, 10 mmol), 0.25 g of the product isolated. Yield 62%; white solid; mp 83-84° C.; 462.0 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ0.82-0.90 (m, 6H), 1.15-1.45 (m, 12H), 1.90-2.05 (m, 4H), 2.86 (brd, J=17.0 Hz, 2H), 3.00 (brd, J=17.0 Hz, 2H), 3.87 (s, 3H), 7.15 (d, J=10.0 Hz, 1H), 7.71 (d, J=10.0 Hz, 1H), 9.20 (brs, 1H), 10.90 (brs, 1H); IR (KBr, cm−1): 3344s, 3208m, 2930m, 2870m, 1677s, 1592s;

Workup

customisolated

Sources & evidence

ORD record: ord-44d3d1ed866b4a2fa2d8980d1e142b89
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331563B1

Reaction notes

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