Diisopropylethylamine → 2-(3-Fluoro-5-((4-(5-methylthiophen-2-ylsulfonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)ethanol

HRID 471132ノート

反応式

HRID 471132 の反応式
[CH3:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[O:11]1[C:16]2([CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:24]=[C:25]([CH2:30][CH2:31][OH:32])[CH:26]=[C:27]([F:29])[CH:28]=3)[CH2:18][CH2:17]2)[CH2:15][NH:14][CH2:13][CH2:12]1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[F:29][C:27]1[CH:26]=[C:25]([CH2:30][CH2:31][OH:32])[CH:24]=[C:23]([CH2:22][N:19]2[CH2:18][CH2:17][C:16]3([O:11][CH2:12][CH2:13][N:14]([S:7]([C:5]4[S:6][C:2]([CH3:1])=[CH:3][CH:4]=4)(=[O:9])=[O:8])[CH2:15]3)[CH2:21][CH2:20]2)[CH:28]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 124001125-Methylthiophene-2-sulfonyl chlorideHCID 579889902-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-5-fluorophenyl)ethanol

生成物 1

HCID 579888972-(3-Fluoro-5-((4-(5-methylthiophen-2-ylsulfonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)ethanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 5-methylthiophene-2-sulfonyl chloride (0.15 g) in DCM (3 mL) was added dropwise to a solution of 2-(3-(1-oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-5-fluorophenyl)ethanol (example 55, step c) (0.21 g) and N-ethyl-N-isopropylpropan-2-amine (0.14 mL) in DCM (20 mL). The resulting mixture was stirred for 1 h and the solvent evaporated. The residue was partitioned between ethyl acetate (50 mL) and saturated sodium hydrogen carbonate solution (50 mL). The layers were separated and the aqueous extracted with ethyl acetate (2×50 mL). The combined organics were washed with brine (50 mL), dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 47.5:47.5:5 ethyl acetate:isohexane:triethylamine to 95:5 ethyl acetate:triethylamine gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow gum. Yield 0.21 g.

後処理

  1. customthe solvent evaporated
  2. customThe residue was partitioned between ethyl acetate (50 mL) and saturated sodium hydrogen carbonate solution (50 mL)
  3. customThe layers were separated
  4. extractionthe aqueous extracted with ethyl acetate (2×50 mL)
  5. washThe combined organics were washed with brine (50 mL)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 47.5:47.5:5 ethyl acetate
  11. additionThe fractions containing product
  12. customevaporated

出典と根拠

ORDレコード
ord-7884015c628b42f7b95adf9162665289
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

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