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

HRID 1011550ノート

反応式

HRID 1011550 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 31214Ethyl orthoformate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e0090dc6e1af461d8c69d440d7a7ef16
出典データセット
uspto-grants-2011_07
特許番号
US07977362B2

反応ノート

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