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 471061노트

반응식

HRID 471061 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d4712536aa6b4af78b43fb81d8a8904d
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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