Sodium Methoxide → (2-{[1-(Methoxycarbonyl)cyclohexyl]thio}-1,3-thiazol-4-yl)acetic acid

HRID 914527노트

반응식

HRID 914527 반응식
[SH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:6]=1.[CH3:11][O:12][C:13]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1Br)=[O:14].C[O-].[Na+]>CO>[CH3:11][O:12][C:13]([C:15]1([S:1][C:2]2[S:3][CH:4]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:6]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14]

참가 물질

5

반응물 3

HCID 10942334Sodium MethoxideHCID 21285841Methyl 2-bromocyclohexane-1-carboxylateHCID 178525233HCID 178525233, 화합물

생성물 1

HCID 59759052(2-{[1-(Methoxycarbonyl)cyclohexyl]thio}-1,3-thiazol-4-yl)acetic acid수율 10.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(2-Mercapto-1,3-thiazol-4-yl)acetic acid (3.50 g) synthesized in Reference Example 51 and 2-bromocyclohexanecarboxylic acid methyl ester (4.42 g) were dissolved in methanol (180 mL), sodium methoxide (2.38 g) was added and the mixture was heated under reflux for 22 hr. The solvent was evaporated, and diethyl ether (50 mL) and water (50 mL) were added to the residue. After stirring, the aqueous layer was obtained by partitioning and adjusted to about pH 4 with 1 mol/L hydrochloric acid. The mixture was extracted with ethyl acetate (100 mL), and the organic layer was washed with saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=3:2 to 0:1) and the obtained solid was washed by suspending in hexane-ethyl acetate to give the title compound (663 mg).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 22 hr
  3. customThe solvent was evaporated
  4. additiondiethyl ether (50 mL) and water (50 mL) were added to the residue
  5. customthe aqueous layer was obtained
  6. customby partitioning
  7. extractionThe mixture was extracted with ethyl acetate (100 mL)
  8. washthe organic layer was washed with saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated
  11. customthe residue was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=3:2 to 0:1)
  12. washthe obtained solid was washed

출처 및 근거

ORD 기록
ord-a13e3c8fad1a49208dfeb9697d6165cd
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026370B2

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