Cyclopentanecarbonyl chloride → (2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-cyclopentylethanone

HRID 448074노트

반응식

HRID 448074 반응식
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:7]=1[CH3:13])[CH2:3][CH2:4][CH3:5].[CH:14]1([C:19](Cl)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C1C=CN=CC=1)C>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:19]([CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:20])[CH2:3][CH2:4][CH3:5]

참가 물질

4

반응물 2

HCID 78284Cyclopentanecarbonyl chlorideHCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

생성물 1

HCID 69188133(2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-cyclopentylethanone

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

실험 절차

In a 20 mL vial 3-butyl-2,4,5-trimethylthiazol-3-ium iodide (48 mg in 0.5 mL DMA, 0.16 mmol, 1 equiv.) was added, followed by TEA (38 mg in 0.5 mL DMA, 0.37 mmol, 2.4 equiv.) and the solution went black. DMAP (2 mg in 0.5 mL DMA, 0.016 mmol, 0.1 equiv) was added next, followed by cyclopentanecarbonyl chloride (0.9 mL of 0.2M in DMA, 1.2 equiv). The mixture was shaken overnight at room temperature and then concentrated in vacuo. The resulting residue was taken up in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.88-0.97 (m, 3 H) 1.30-1.39 (m, 2 H) 1.51-1.62 (m, 4 H) 1.62-1.70 (m, 3 H) 1.77-1.87 (m, 2 H) 2.16-2.26 (m, 5 H) 2.73-2.86 (m, 1 H) 3.71-3.83 (m, 4 H) 5.84-5.94 (m, 1 H); MS (ESI) m/z 280 (M+H)+.

후처리

  1. concentrationconcentrated in vacuo
  2. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-f4b71200f4094190830905d60b361090
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481574B2

반응 노트

불러오는 중…