홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Sodium Chlorite → 3-[4-(Benzenesulfonylmethyl)-3-tert-butoxycarbonyl-2-hydroxyphenyl]-furan-2-carboxylic acid

HRID 1778349
노트
인쇄 미리보기

반응식

HRID 1778349 반응식
OP([O-])(O)=O.[Na+].[C:7]1([S:13]([CH2:16][C:17]2[C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:21]([OH:30])[C:20]([C:31]3[CH:35]=[CH:34][O:33][C:32]=3[CH:36]=[O:37])=[CH:19][CH:18]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl([O-])=[O:39].[Na+]>O.C(#N)C.OO>[C:7]1([S:13]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:31]3[CH:35]=[CH:34][O:33][C:32]=3[C:36]([OH:39])=[O:37])=[C:21]([OH:30])[C:22]=2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 23668197Sodium Chlorite2회HCID 23672064Monosodium phosphate2회HCID 86684731Tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate2회

생성물 1

HCID 666926633-[4-(Benzenesulfonylmethyl)-3-tert-butoxycarbonyl-2-hydroxyphenyl]-furan-2-carboxylic acid수율 25.7%

시약·촉매·용매 3

HCID 784
Hydrogen Peroxide
용매
2회
HCID 962Water용매2회
HCID 6342Acetonitrile용매

실험 절차

A solution of sodium phosphate monobasic (0.039 g) in water (1 mL) was added to a solution of tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate (Intermediate 27, 0.105 g) in acetonitrile (2 mL) at 0° C. Hydrogen peroxide (50% wt. in water, 0.078 mL) and sodium chlorite (0.029 g) were added and the reaction mixture was warmed to room temperature and stirred for 18 hours. The mixture was cooled to 0° C. and further sodium phosphate monobasic (0.028 g) in water (0.5 mL), hydrogen peroxide (50% wt. in water, 0.038 mL) and sodium chlorite (0.052 g) were added and the mixture was warmed to room temperature and stirred for 18 hours. The mixture was poured onto sodium sulfite (10% in water) at 0° C., extracted into ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and 1% acetic acid in methanol with a gradient of O-100%. The resultant product was triturated in cyclohexane and ethyl acetate and the solid was collected by filtration and dried in vacuo to give 3-[4-(benzenesulfonylmethyl)-3-tert-butoxycarbonyl-2-hydroxy-phenyl]-furan-2-carboxylic acid (0.028 g) as a white solid.

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. temperaturethe mixture was warmed to room temperature
  3. stirringstirred for 18 hours
  4. additionThe mixture was poured onto sodium sulfite (10% in water) at 0° C.
  5. extractionextracted into ethyl acetate
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was purified by chromatography on silica
  11. washeluting with a mixture of methanol and 1% acetic acid in methanol with a gradient of O-100%
  12. customThe resultant product was triturated in cyclohexane
  13. filtrationethyl acetate and the solid was collected by filtration
  14. customdried in vacuo

출처 및 근거

ORD 기록
ord-3a95b30ccf604127ad147b642f99b05a
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266896B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트