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

HRID 471132노트

반응식

HRID 471132 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7884015c628b42f7b95adf9162665289
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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