Trifluoroacetic acid → 2-Fluoro-2-(3-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

HRID 1689292ノート

反応式

HRID 1689292 の反応式
[F:1][CH:2]([C:5]1[CH:6]=[C:7]([CH:30]=[CH:31][CH:32]=1)[CH2:8][N:9]1[CH2:29][CH2:28][C:12]2([O:17][CH2:16][CH2:15][N:14]([C:18]([C:20]3[N:21]=[C:22]([CH:25]([CH3:27])[CH3:26])[S:23][CH:24]=3)=[O:19])[CH2:13]2)[CH2:11][CH2:10]1)[CH2:3][OH:4].FC(F)(F)C(O)=O.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][CH:2]([C:5]1[CH:32]=[CH:31][CH:30]=[C:7]([CH2:8][N:9]2[CH2:29][CH2:28][C:12]3([O:17][CH2:16][CH2:15][N:14]([C:18]([C:20]4[N:21]=[C:22]([CH:25]([CH3:26])[CH3:27])[S:23][CH:24]=4)=[O:19])[CH2:13]3)[CH2:11][CH2:10]2)[CH:6]=1)[CH:3]=[O:4]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 67292595(9-(3-(1-Fluoro-2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

生成物 1

HCID 579890482-Fluoro-2-(3-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (9-(3-(1-fluoro-2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 39, step f) (0.213 g) in DCM (5 mL) was cooled in ice-water and treated with trifluoroacetic acid (0.053 mL) and stirred for 5 minutes. Dess-Martin periodinane (0.296 g) was added and the mixture was removed from the cooling bath and stirred at room temperature for 20 minutes. More Dess-Martin periodinane (0.295 g) was added and the mixture was stirred at room temperature for an additional 30 minutes. The reaction was then quenched by the addition of saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (5 mL), and the resulting two-phase mixture was stirred for 10 minutes. The mixture was then extracted twice with ethyl acetate, and the combined organic extracts washed with brine. Acetic acid (0.1 mL) was added, then the acidified extracts were dried over anhydrous magnesium sulphate and concentrated in vacuo to afford the crude subtitled product as an off-white foam. Yield 0.240 g.

後処理

  1. customthe mixture was removed from the cooling bath
  2. stirringstirred at room temperature for 20 minutes
  3. additionMore Dess-Martin periodinane (0.295 g) was added
  4. stirringthe mixture was stirred at room temperature for an additional 30 minutes
  5. customThe reaction was then quenched by the addition of saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (5 mL)
  6. stirringthe resulting two-phase mixture was stirred for 10 minutes
  7. extractionThe mixture was then extracted twice with ethyl acetate
  8. washthe combined organic extracts washed with brine
  9. additionAcetic acid (0.1 mL) was added
  10. dry with materialthe acidified extracts were dried over anhydrous magnesium sulphate
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-65442db1a4dd40cab6f3fd8ba70c1c60
出典データセット
uspto-grants-2012_04
特許番号
US08148373B2

反応ノート

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