Hydroxylamine → HCID 18678884, compound

HRID 1634702Notes

Reaction equation

HRID 1634702 reaction equation
[NH2:1][OH:2].[Cl:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][N:9]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:10][CH2:11][C:12](OCC)=[O:13])=[CH:6][CH:5]=1>>[OH:2][NH:1][C:12](=[O:13])[CH2:11][CH2:10][N:9]([CH2:8][C:7]1[CH:28]=[CH:29][C:4]([Cl:3])=[CH:5][CH:6]=1)[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18]

Participants

3

Reactant 2

HCID 787HydroxylamineHCID 18678868HCID 18678868, compound

Product 1

HCID 18678884HCID 18678884, compoundYield 80%

Procedure

Freshly prepared NH2OH solution (1 M in methanol) (0.2 mL, 0.2 mmol) was added to ethyl 3-[(4-chlorobenzyl)-(4-methoxybenzenesulfonyl)-amino]-propionate (44 mg, 0.1 mmol). After being stirred at room temperature for 18 h, the reaction mixture was concentrated. The crude product was triturated in ether and the residue was lyophilized from water to give N-hydroxy-3-[(4-chlorobenzyl)-(4-methoxybenzene-sulfonyl)-amino]-propionamide (30 mg, 0.08 mmol) as a light yellow solid. 1H-NMR (360 MHz, DMSO-d6) δ 7.75 (d, J=8.8 Hz, 2H), 7.39 (d, J=8.5 Hz, 2H), 7.32 (d, J=8.4 Hz, 2H), 7.11 (d, J=8.8 Hz, 2H), 4.28 (s, 2H), 3.85 (s, 3H), 3.20 (br t, J=7.8 Hz, 2H), 1.86 (t, J=8.1 Hz, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe crude product was triturated in ether

Sources & evidence

ORD record
ord-b9d1deea20d74bd78905802f6dd35955
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

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