Water → methyl N-(5-but-3-en-1-yl-1,3,4-oxadiazol-2-yl)-L-valinate

HRID 1924379ノート

反応式

HRID 1924379 の反応式
[C:1]([NH:7][NH:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])(=O)[CH2:2][CH2:3][CH:4]=[CH2:5].O.C([O-])(O)=O.[Na+]>O=P(Cl)(Cl)Cl>[CH2:2]([C:1]1[O:10][C:9]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])=[N:8][N:7]=1)[CH2:3][CH:4]=[CH2:5]

参加物

5

反応物 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 44549344methyl N-[(2-pent-4-enoylhydrazino)carbonyl]-L-valinate

生成物 1

HCID 67519434methyl N-(5-but-3-en-1-yl-1,3,4-oxadiazol-2-yl)-L-valinate

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

反応条件

温度
0 °C

実験手順

Methyl N-[(2-pent-4-enoylhydrazino)carbonyl]-L-valinate (from Step 3) was heated at 80° C. for 2 h in POCl3 (0.1 M solution). The mixture was cooled at 0° C. and water was carefully added. Solid NaHCO3 was added until the mixture reached pH 7, then the mixture was extracted with EtOAc and the organic layer dried over Na2SO4 to obtain a pale yellow oil. 1H NMR (400 MHz, DMSO-d6) δ: 8.42 (d, J 15.7, 1H), 5.88-5.78 (m, 1H), 5.08 (d, J 17.2, 1H), 5.01 (d, J 10.3, 1H), 4.04 (dd, J 7.1, 14.2, 1H), 3.64 (s, 3H), 2.75 (t, J 7.3, 2H), 2.39 (m, 2H), 2.13-2.06 (m, 1H), 0.94 (d, J 3.9, 3H), 0.92 (d, J 3.9, 3H). MS (ES+) C12H19N3O3 requires: 253 found: 254 (M+H+).

後処理

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialthe organic layer dried over Na2SO4
  3. customto obtain a pale yellow oil

出典と根拠

ORDレコード
ord-34283cb695d8482d8e4f500ead1b907c
出典データセット
uspto-grants-2012_05
特許番号
US08178520B2

反応ノート

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