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Lithium Hydroxide → cis-(1aRS,7bSR)-5-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylmethyl]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid

HRID 59665
ノート
印刷プレビュー

反応式

HRID 59665 の反応式
[CH2:1]([N:3]([CH2:33][CH3:34])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([CH2:17][C:18]1[C:27]([C:28]([O:30]C)=[O:29])=[C:26]2[C:21]([C@H:22]3[CH2:32][C@H:23]3[CH2:24][O:25]2)=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:2].[OH-].[Li+]>O1CCOCC1.O>[CH2:33]([N:3]([CH2:1][CH3:2])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([CH2:17][C:18]1[C:27]([C:28]([OH:30])=[O:29])=[C:26]2[C:21]([C@H:22]3[CH2:32][C@H:23]3[CH2:24][O:25]2)=[CH:20][CH:19]=1)(=[O:15])=[O:16])[CH3:34]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 131737059methyl cis-(1aRS,7bSR)-5-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylmethyl]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2 回

生成物 1

HCID 71664454cis-(1aRS,7bSR)-5-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylmethyl]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid収率 17.9%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A mixture of methyl cis-(1aRS,7bSR)-5-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluoro-benzenesulfonylmethyl]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 1, 0.72 g) and lithium hydroxide (0.622 g) in dioxane (20 mL) and water (5 mL) was stirred and heated at 80° C. for 5 hours. After cooling, the mixture was filtered and the filtrate was concentrated to low volume under vacuum. The aqueous residue was acidified with formic acid to pH 5 and extracted with DCM. The organic layer was dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by reverse phase chromatography using a C-18 5 micron cartridge and eluting with a mixture of methanol and water, with a gradient of 10-98%. The product was repurified by HPLC(C18) eluting with a mixture of acetonitrile and water (containing 0.1% formic acid) to give cis-(1aRS,7bSR)-5-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylmethyl]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid (0.125 g) as a white solid.

後処理

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated to low volume under vacuum
  4. extractionextracted with DCM
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by reverse phase chromatography
  9. washeluting with a mixture of methanol and water, with a gradient of 10-98%
  10. customThe product was repurified by HPLC(C18)
  11. washeluting with a mixture of acetonitrile and water (containing 0.1% formic acid)

出典と根拠

ORDレコード
ord-61415556f31444728857e3e2fa13b693
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09440943B2

反応ノート

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