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Acetic Acid → (Z)-7-{(1R,2S)-2-[(E)-(S)-5-(4-Bromo-5-methyl-thiophen-2-yl)-3-hydroxy-pent-1-enyl]-5-oxo-cyclopent-3-enyl}-hept-5-enoic acid methyl ester

HRID 1042369
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인쇄 미리보기

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HRID 1042369 반응식
[CH3:1][O:2][C:3](=[O:44])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]1[C:14](=[O:15])[CH2:13][C@@H:12](O[Si](C(C)(C)C)(C)C)[C@@H:11]1/[CH:24]=[CH:25]/[C@@H:26]([O:36][Si](C(C)(C)C)(C)C)[CH2:27][CH2:28][C:29]1[S:30][C:31]([CH3:35])=[C:32]([Br:34])[CH:33]=1.CC(O)=O.O.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:44])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]1[C:14](=[O:15])[CH:13]=[CH:12][C@@H:11]1/[CH:24]=[CH:25]/[C@@H:26]([OH:36])[CH2:27][CH2:28][C:29]1[S:30][C:31]([CH3:35])=[C:32]([Br:34])[CH:33]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 67092628(Z)-7-[(1R,2R,3R)-2-[(E)-(S)-5-(4-Bromo-5-methyl-thiophen-2-yl)-3-(tert-butyl-dimethyl-silanyloxy)-pent-1-enyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-hept-5-enoic acid methyl ester

생성물 1

HCID 67092554
(Z)-7-{(1R,2S)-2-[(E)-(S)-5-(4-Bromo-5-methyl-thiophen-2-yl)-3-hydroxy-pent-1-enyl]-5-oxo-cyclopent-3-enyl}-hept-5-enoic acid methyl ester
수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

A mixture of 5 (1.486 g, 2.03 mmol), HOAc (20 mL), H2O (10 mL) and THF (10 mL) was stirred at 70° C. for 17 h. The reaction was then poured into 750 mL saturated NaHCO3 solution and the resulting mixture was extracted with ethyl acetate (4×200 mL). The combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated. Flash chromatography (50% ethyl acetate/hexanes) gave 6 (497 mg, 1.03 mmol, 51%).

후처리

  1. extractionthe resulting mixture was extracted with ethyl acetate (4×200 mL)
  2. dry with materialThe combined ethyl acetate solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

출처 및 근거

ORD 기록
ord-ff9310c5d76d454f98e8add541efa87f
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08557860B2

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