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Sodium hydride → Rac-3-{1-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1h-indol-4-yl}-2-ethoxy-propionic acid ethyl ester

HRID 11382
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HRID 11382 반응식
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:21])[CH:7]([O:18][CH2:19][CH3:20])[CH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)[CH3:4].Cl[CH2:23][C:24]1[N:25]=[C:26]([C:30]2[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([O:38][CH3:39])[CH:31]=2)[O:27][C:28]=1[CH3:29]>CN(C)C=O.O>[CH2:3]([O:5][C:6](=[O:21])[CH:7]([O:18][CH2:19][CH3:20])[CH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:23][C:24]1[N:25]=[C:26]([C:30]2[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([O:38][CH3:39])[CH:31]=2)[O:27][C:28]=1[CH3:29])[CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 21974252Oxazole, 4-(chloromethyl)-2-(3,5-dimethoxyphenyl)-5-methyl-HCID 69279879Rac-2-ethoxy-3-(1h-indol-4-yl)-propionic acid ethyl ester

생성물 1

HCID 69279866Rac-3-{1-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1h-indol-4-yl}-2-ethoxy-propionic acid ethyl ester수율 84%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

실험 절차

0.048 g (1.10 mmol) Sodium hydride (55% in mineral oil) was added in one portion below 5° C. and under argon to a stirred solution of 0.261 g (1.00 mmol) rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester and 0.321 g (1.20 mmol) 4-chloromethyl-2-(3,5-dimethoxy-phenyl)-5-methyl-oxazole in 15.0 ml N,N-dimethylformamide. The reaction mixture was warmed up to room temperature and then stirred for 16 hours at ambient temperature. It was then diluted with cold water and extracted two times with ethyl acetate. The combined organic phases were dried over MgSO4, filtered and evaporated. The residue formed was purified by flash-chromatography (silica gel; eluent: gradient of hexane and ethyl acetate) to give 0.413 g (84%) rac-3-{1-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1H-indol-4-yl}-2-ethoxy-propionic acid ethyl ester as light yellow solid.

후처리

  1. extractionextracted two times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue formed
  6. customwas purified by flash-chromatography (silica gel; eluent: gradient of hexane and ethyl acetate)

출처 및 근거

ORD 기록
ord-2bbd1173503f43e4a80adb2b4bc005c0
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07098228B2

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