1-Nonanol, 9-bromo- → (9-(9-Hydroxynonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

HRID 1689186노트

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HRID 1689186 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].Cl.[CH3:13][C:14]1[S:15][CH:16]=[C:17]([C:19]([N:21]2[CH2:26][C:25]3([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[O:24][CH2:23][CH2:22]2)=[O:20])[N:18]=1>C(N(CC)CC)C.C(#N)C>[OH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:29]1[CH2:30][CH2:31][C:25]2([O:24][CH2:23][CH2:22][N:21]([C:19]([C:17]3[N:18]=[C:14]([CH3:13])[S:15][CH:16]=3)=[O:20])[CH2:26]2)[CH2:27][CH2:28]1

참가 물질

5

반응물 2

HCID 1087001-Nonanol, 9-bromo-HCID 67291637(2-Methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone hydrochloride

생성물 1

HCID 46240299(9-(9-Hydroxynonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

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온도
50 °C

실험 절차

9-Bromononan-1-ol (0.29 g) was added to a suspension of (2-methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone hydrochloride (example 1, step f) (0.4 g) in a mixture of triethylamine (0.41 mL) and acetonitrile (10 mL). The resulting mixture was stirred for 16 h at 50° C. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate (30 mL) and saturated sodium bicarbonate solution (30 mL). The layers were separated and the aqueous extracted with ethyl acetate (2×30 mL). The combined organic solutions were washed with brine (30 mL), dried over sodium sulphate, filtered and evaporated in vacuo. The residue was dissolved in methanol (10 mL) and applied to a SCX cartridge pre-wetted with methanol. The cartridge was washed with methanol (10 mL) and eluted with 3M ammonia in methanol solution (100 mL). The eluent was evaporated in vacuo to give the subtitled compound a yellow oil. Yield 0.32 g.

후처리

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between ethyl acetate (30 mL) and saturated sodium bicarbonate solution (30 mL)
  3. customThe layers were separated
  4. extractionthe aqueous extracted with ethyl acetate (2×30 mL)
  5. washThe combined organic solutions were washed with brine (30 mL)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. dissolutionThe residue was dissolved in methanol (10 mL)
  10. washThe cartridge was washed with methanol (10 mL)
  11. washeluted with 3M ammonia in methanol solution (100 mL)
  12. customThe eluent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-fd9a60e9d0dd4b2eb8a148c43a4b4ca3
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

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