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

HRID 489633노트

반응식

HRID 489633 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 178456097HCID 178456097, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
150 °C

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-1cf0b383d0694fd8a2cfa9cae0221e8a
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977256B2

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