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

HRID 470955ノート

反応式

HRID 470955 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aae94472ae214b43868af37443af4f05
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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