Cuminaldehyde → [Rac]-2-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-5,6,7,8-tetrahydro-naphthalen-1-yl}-propionic acid ethyl ester

HRID 479179노트

반응식

HRID 479179 반응식
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:23])[CH:7]([O:20][CH2:21][CH3:22])[CH2:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[C:12]([OH:19])=[CH:11][CH:10]=1)[CH3:4].Cl[CH2:25][C:26]1[N:27]=[C:28]([C:32]2[CH:37]=[CH:36][C:35]([CH:38]([CH3:40])[CH3:39])=[CH:34][CH:33]=2)[O:29][C:30]=1[CH3:31].C(C1C=CC(C=O)=CC=1)(C)C.O=P(Cl)(Cl)Cl>CN(C)C=O.O>[CH2:3]([O:5][C:6](=[O:23])[CH:7]([O:20][CH2:21][CH3:22])[CH2:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[C:12]([O:19][CH2:25][C:26]2[N:27]=[C:28]([C:32]3[CH:33]=[CH:34][C:35]([CH:38]([CH3:40])[CH3:39])=[CH:36][CH:37]=3)[O:29][C:30]=2[CH3:31])=[CH:11][CH:10]=1)[CH3:4]

참가 물질

8

반응물 5

HCID 326CuminaldehydeHCID 24758Sodium hydrideHCID 24813Phosphorus oxychlorideHCID 219742554-(Chloromethyl)-2-(4-isopropylphenyl)-5-methyloxazoleHCID 69557425[Rac]-2-ethoxy-3-(4-hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-propionic acid ethyl ester

생성물 1

HCID 69557022[Rac]-2-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-5,6,7,8-tetrahydro-naphthalen-1-yl}-propionic acid ethyl ester수율 67.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

0.037 g (1.54 mmol) Sodium hydride was added in small portions below 30° C. and under argon to a solution of 0.30 g (1.03 mmol) [rac]-2-ethoxy-3-(4-hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-propionic acid ethyl ester in 5.0 ml N,N-dimethylformamide. After 10 minutes, 0.384 g (1.54 mmol) 4-chloromethyl-2-(4-isopropyl-phenyl)-5-methyl-oxazole (prepared from 4-isopropyl-benzaldehyde and diacetyl monoxyme followed by treatment with POCl3 in analogy to the procedures described in examples 21 a] and b]) were added and the reaction mixture then stirred for 16 hours at ambient temperature. It was then diluted with water and extracted with ether. The combined organic phases were dried over MgSO4 and evaporated. The residue formed was purified by flash-chromatography (silica gel; eluent: gradient of hexane and ethyl acetate) to give 0.35 g (67%) of [rac]-2-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-5,6,7,8-tetrahydro-naphthalen-1-yl}-propionic acid ethyl ester as colorless oil.

후처리

  1. additionwere added
  2. extractionextracted with ether
  3. dry with materialThe combined organic phases were dried over MgSO4
  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-aab6d2ce9a0746aa989c9f03e29c7046
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642389B2

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