Hydroxylamine → tert-Butyl (3S,4R)-3-[(hydroxyamino)carbonyl]-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]piperidine-1-carboxylate

HRID 736753Notes

Reaction equation

HRID 736753 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=[C:28]([CH3:36])[CH:27]=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:10]([C:37]([OH:39])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:40][OH:41]>>[OH:41][NH:40][C:37]([C@@H:10]1[C@H:11]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=[C:28]([CH3:36])[CH:27]=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9]1)=[O:39]

Participants

3

Reactant 2

HCID 787HydroxylamineHCID 688188354-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

Product 1

HCID 11855330tert-Butyl (3S,4R)-3-[(hydroxyamino)carbonyl]-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]piperidine-1-carboxylate

Procedure

According to the procedure of Example 24, Step 3, 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (0.17 g, 0.30 mmol) and hydroxylamine gave a 7:1 mixture of cis- and trans-tert-Butyl (3S,4R)-3-[(hydroxyamino)carbonyl]-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]piperidine-1-carboxylate as an amorphous white solid (0.025 g, 14.6%) after purification using Biotage Flash 40S chromatography, eluting with 5% methanol in ethyl acetate. Mass Spectrum Found: 571 (M+H)+

Workup

  1. customgave
  2. customafter purification
  3. washeluting with 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-9c358b7aaf5b4ebd952249815549b111
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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