Methanol → tert-butyl N-[2-(1,2,4-oxadiazol-3-yl)propan-2-yl]carbamate

HRID 632082ノート

反応式

HRID 632082 の反応式
[NH2:1]/[C:2](=[N:14]\[OH:15])/[C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:5])[CH3:4].[CH2:16](OC(OCC)OCC)C.FC(F)(F)C(O)=O.CO>C(#N)C.O>[O:15]1[CH:16]=[N:1][C:2]([C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])([CH3:5])[CH3:4])=[N:14]1

参加物

7

反応物 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 31214Ethyl orthoformateHCID 61324195tert-butyl N-[1-(N'-hydroxycarbamimidoyl)-1-methylethyl]carbamate

生成物 1

HCID 73357654tert-butyl N-[2-(1,2,4-oxadiazol-3-yl)propan-2-yl]carbamate収率 32%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To a solution of (Z)-tert-butyl 1-amino-1-(hydroxyimino)-2-methylpropan-2-ylcarbamate (Example 33 b, 2 g, 9.2 mmol) in acetonitrile (10 mL) was added triethoxymethane (CAN 122-51-0, 4.8 mL) and trifluoroacetic acid (CAN 76-05-1, 0.1 mL). The mixture was heated to 50° C. and stirred overnight. The reaction mixture was added to methanol (10 mL) and water (10 mL). After evaporation of solvents, the residue was purified by column chromatography (silica gel, 60 g, eluting with 30% to 50% ethyl acetate in petroleum ether) to give the target product (0.668 g, 32%) MS (EI): m/e=250.1 [M+H]+.

後処理

  1. customAfter evaporation of solvents
  2. customthe residue was purified by column chromatography (silica gel, 60 g, eluting with 30% to 50% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-264ec10aeb0f4f098f0f3ff478dea8d2
出典データセット
uspto-grants-2016_04
特許番号
US09321727B2

反応ノート

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