Hydroxylamine → HCID 9865362, compound

HRID 1634706Notes

Reaction equation

[NH2:1][OH:2].[CH3:3][O:4][C:5]1[CH:29]=[CH:28][C:8]([CH2:9][CH2:10][N:11]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=2)(=[O:20])=[O:19])[CH2:12][CH2:13][C:14](OC)=[O:15])=[CH:7][CH:6]=1>>[OH:2][NH:1][C:14](=[O:15])[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:29][CH:28]=1)[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=1)(=[O:20])=[O:19]

Participants

Reactant 2

HCID 787Hydroxylamine

HCID 18678888HCID 18678888, compound

Product 1

HCID 9865362HCID 9865362, compoundYield 28.6%

Procedure

Freshly prepared NH2OH solution (1 M in MeOH) (0.6 mL, 0.6 mmol)) was added to methyl 3-[(4-methoxyphenethyl)-(3-aminobenzenesulfonyl)amino]propionate (110 mg, 0.28 mmol). After stirring at room temperature for 18 h, the reaction mixture was concentrated and taken up with 10 mL of water. The mixture was acidified to pH 3-4 by 1 N HCl solution and extracted with ethyl acetate (2×20 mL). Combined organic layers was washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel chromatography (10/1 methylene chloride/methanol) to give N-hydroxy-3-[(4-methoxyphenethyl)-(3-aminobenzene-sulfonyl)amino]-propionamide (33 mg, 0.08 mmol). NMR (360 MHz, DMSO-d6) δ 10.44 (s, 1H), 8.72 (br s, 1H), 7.23-6.25 (m, 8H), 5.57 (br s, 2H), 3.70 (s, 3H), 3.33 (t, 2H), 3.24 (t, 2H), 2.65 (t, 2H), 2.24 (t, 2H).

Workup

concentrationthe reaction mixture was concentrated
extractionextracted with ethyl acetate (2×20 mL)
washCombined organic layers was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by silica gel chromatography (10/1 methylene chloride/methanol)

Sources & evidence

ORD record: ord-81254c1d4bb54f85a0c247ca23e7aedf
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506936B1

Reaction notes

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