Hydroxylamine → n-(4-(1,2,4-Oxadiazol-3-yl)benzyl)-n-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide

HRID 1011550Notes

Reaction equation

HRID 1011550 reaction equation
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]([CH:19]2[CH2:24][CH:23]3[CH:25]([OH:26])[CH:20]2[CH2:21][CH2:22]3)[S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[NH2:29]O.C([O:34][CH2:35]C)(=O)C>C(O)C.C(OC(OCC)OCC)C>[O:34]1[CH:35]=[N:29][C:1]([C:3]2[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH:19]3[CH2:24][CH:23]4[CH:25]([OH:26])[CH:20]3[CH2:21][CH2:22]4)[S:9]([C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)(=[O:11])=[O:10])=[CH:27][CH:28]=2)=[N:2]1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 8857Ethyl AcetateHCID 59497811N-(4-cyanobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide

Product 1

HCID 59497796n-(4-(1,2,4-Oxadiazol-3-yl)benzyl)-n-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamideYield 44%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 31214Ethyl orthoformateSolvent

Procedure

A mixture of N-(4-cyanobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide (380 mg, 0.91 mmol) and hydroxylamine (500 up was refluxed in 20 mL ethanol for 2 h. The reaction was concentrated and dried under high vacuum. A portion of the crude amide oxime (25 mg) which was obtained was refluxed in triethylorthoformate (2 mL) for 5 h. The reaction was diluted into 20 mL ethyl acetate, washed with brine, and purified by flash chromatography on 4 g silica gel with 0 to 30% ethyl acetate in hexane to yield N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide (11 mg, 44%). 1H NMR (400 MHz, CDCl3) δ ppm 8.73 (1H, s), 8.00-8.08 (2H, m), 7.68-7.79 (2H, m), 7.40-7.49 (4H, m), 4.83 (2H, q, J=17.54 Hz), 4.02-4.11 (1H, m), 3.83 (1H, s), 1.88 (1H, br. s.), 1.58-1.68 (2H, m), 1.43-1.55 (3H, m), 1.06-1.16 (2H, m). LC/MS R.T.=2.35 min; [M+H]+=460.13.

Workup

  1. concentrationThe reaction was concentrated
  2. customdried under high vacuum
  3. customA portion of the crude amide oxime (25 mg) which was obtained
  4. washwashed with brine
  5. custompurified by flash chromatography on 4 g silica gel with 0 to 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e0090dc6e1af461d8c69d440d7a7ef16
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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