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Cesium carbonate → HCID 68867360, 화합물

HRID 1985180
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HRID 1985180 반응식
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[CH3:23][C:24]1[CH:52]=[CH:51][C:27]([CH2:28][N:29]2[CH2:33][CH:32]([CH2:34][CH2:35]OS(C3C=CC(C)=CC=3)(=O)=O)[N:31]([CH2:47][CH2:48][CH3:49])[C:30]2=[O:50])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:35][CH2:34][CH:32]2[CH2:33][N:29]([CH2:28][C:27]3[CH:51]=[CH:52][C:24]([CH3:23])=[CH:25][CH:26]=3)[C:30](=[O:50])[N:31]2[CH2:47][CH2:48][CH3:49])=[CH:9][CH:8]=1)[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 11220314Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionateHCID 57719317HCID 57719317, 화합물

생성물 1

HCID 68867360HCID 68867360, 화합물수율 68.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

A mixture of 3-(4-hydroxy-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (0.80 g, 2.66 mmol), toluene-4-sulfonic acid 2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethyl ester (1.26 g, 2.93 mmol) and Cs2CO3 (1.04 g, 3.19 mmol) in DMF (40 mL) is heated to 55° C. under N2 for 17 h. The reaction is cooled and quenched with 1 N HCl (20 mL) and worked up extractively with Et2O and water. The organic layer is dried and the solvent removed to afford crude product that is purified by flash chromatography using 7:1 hexanes:acetone to afford 1.02 g (68%) 2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester. The diasteriomeric products were separated by chiral HPLC (90:10 heptane:IPA, 280 mL/min, 220 nm,) to give products in >99% de. Rf=0.49 (1:1 acetone:hexanes). 1H NMR. MS (ES+) Calc'd for C34H43N2O5 (M+1) 559. Found m/z 559 (100%).

후처리

  1. temperatureThe reaction is cooled
  2. customquenched with 1 N HCl (20 mL)
  3. customThe organic layer is dried
  4. customthe solvent removed
  5. customto afford crude product that
  6. customis purified by flash chromatography

출처 및 근거

ORD 기록
ord-4e5d4890e1904f229732685ea40ba951
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07544812B2

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