Lithium Hydroxide → (1aRS,7bSR)-5-(4-fluoro-2-vinylbenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid

HRID 927960노트

반응식

HRID 927960 반응식
[OH-].[Li+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[C:23]([C:24]([O:26]C)=[O:25])=[C:22]3[C:17]([CH:18]4[CH2:28][CH:19]4[CH2:20][O:21]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[C:6]([CH:29]=[CH2:30])[CH:5]=1>O1CCOCC1.O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[C:23]([C:24]([OH:26])=[O:25])=[C:22]3[C:17]([CH:18]4[CH2:28][CH:19]4[CH2:20][O:21]3)=[CH:16][CH:15]=2)(=[O:11])=[O:12])=[C:6]([CH:29]=[CH2:30])[CH:5]=1

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 86713308methyl (1aRS,7bSR)-5-(4-fluoro-2-vinylbenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2회

생성물 1

HCID 86713253(1aRS,7bSR)-5-(4-fluoro-2-vinylbenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

Lithium hydroxide (0.101 g) was added to a solution of methyl (1aRS,7bSR)-5-(4-fluoro-2-vinylbenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 75, 0.150 g) in a mixture of dioxane (3 mL) and water (0.6 mL) and the mixture was irradiated in the microwave at 130° C. for 30 minutes. After cooling, the mixture evaporated to dryness and the residue was acidified by addition of 10% aqueous citric acid (2 mL), extracted with DCM, 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 DCM with a gradient of 0-10% to give (1aRS,7bSR)-5-(4-fluoro-2-vinylbenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid (0.0.35 g) as a glass.

후처리

  1. customthe mixture was irradiated in the microwave at 130° C. for 30 minutes
  2. temperatureAfter cooling
  3. customthe mixture evaporated to dryness
  4. additionthe residue was acidified by addition of 10% aqueous citric acid (2 mL)
  5. extractionextracted with DCM
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography on silica eluting with a mixture of methanol and DCM with a gradient of 0-10%

출처 및 근거

ORD 기록
ord-06c98e3bcbbd463989e46689c38b6bf3
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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