Triethylamine → {(S)-1-[hydroxy-(5-thiophen-3-yl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-carbamic acid tert-butyl ester

HRID 1765683ノート

反応式

HRID 1765683 の反応式
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([CH:11]([OH:16])[C:12](=[NH:15])[NH:13][OH:14])[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1C(Cl)=O.[CH2:26](N(CC)CC)C>O1CCOCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([CH:11]([OH:16])[C:12]1[N:15]=[C:26]([C:20]2[CH:21]=[CH:22][S:18][CH:19]=2)[O:14][N:13]=1)[CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 178456097HCID 178456097、化合物

生成物 1

HCID 60054516{(S)-1-[hydroxy-(5-thiophen-3-yl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

A suspension of {(S)-1-[hydroxy-(N-hydroxycarbamimidoyl)-methyl]-propyl}-carbamic acid tert-butyl ester (2.4 g, 9.7 mmol) in dioxane (15 ml) was treated with thiophene carbonyl chloride (1.45 g, 9.9 mmol) and triethylamine (1.36 ml, 9.8 mmol) and the mixture heated at 150° C. in a microwave (Smith Creator, S00219) for 15 minutes. Solvent evaporated under reduced pressure. The residue was subjected to flash chromatography eluting with a mixture of ethyl acetate and heptane to give {(S)-1-[hydroxy-(5-thiophen-3-yl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-carbamic acid tert-butyl ester, a mixture of diastereoisomers, (144 mg) as a brown solid. 1H NMR (CDCl3): 8.21 (m, 1H), 7.66 (m, 1H), 7.45 (m, 1H), 4.92–4.69 (m, 2H), 5.02–4.80 (m, 2H), 4.10–3.85 (2×m, 1H), 1.80–1.45 (m, 2H), 1.46 & 1.38 (2×s, 9H), 1.01 & 0.99 (2×t, J=7.5 Hz, 3H). MS: 340 (MH+).

後処理

  1. customSolvent evaporated under reduced pressure
  2. washeluting with a mixture of ethyl acetate and heptane

出典と根拠

ORDレコード
ord-52b00f39a9374a9f964c340e9e422d14
出典データセット
uspto-grants-2007_06
特許番号
US07226921B2

反応ノート

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