Trifluoroacetic acid → 2-(3-Chloro-5-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

HRID 471102노트

반응식

HRID 471102 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([CH2:30][CH2:31][OH:32])[CH:29]=1)[CH2:5][N:6]1[CH2:26][CH2:25][C:9]2([O:14][CH2:13][CH2:12][N:11]([C:15]([C:17]3[N:18]=[C:19]([CH:22]([CH3:24])[CH3:23])[S:20][CH:21]=3)=[O:16])[CH2:10]2)[CH2:8][CH2:7]1.FC(F)(F)C(O)=O.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:29]=[C:28]([CH2:30][CH:31]=[O:32])[CH:27]=[C:4]([CH2:5][N:6]2[CH2:26][CH2:25][C:9]3([O:14][CH2:13][CH2:12][N:11]([C:15]([C:17]4[N:18]=[C:19]([CH:22]([CH3:23])[CH3:24])[S:20][CH:21]=4)=[O:16])[CH2:10]3)[CH2:8][CH2:7]2)[CH:3]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 57989350(9-(3-Chloro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

생성물 1

HCID 579893542-(3-Chloro-5-((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-chloro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 52, step c) (0.242 g) in DCM (5 mL) was cooled in ice-water, treated with trifluoroacetic acid (0.059 mL) and stirred for 5 minutes. Dess-Martin periodinane (0.323 g) was added, then the mixture was removed from the cooling bath and stirred at room temperature for 30 minutes. The solution was diluted with saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (5 mL) and the resulting mixture was stirred vigorously for 10 minutes. The mixture was then extracted twice with ethyl acetate, the combined organic phases were washed with brine, acidified with acetic acid (0.1 mL), dried over anhydrous magnesium sulphate and concentrated in vacuo to give the crude subtitled compound as a yellow foam. Yield 0.297 g.

후처리

  1. customthe mixture was removed from the cooling bath
  2. stirringstirred at room temperature for 30 minutes
  3. additionThe solution was diluted with saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (5 mL)
  4. stirringthe resulting mixture was stirred vigorously for 10 minutes
  5. extractionThe mixture was then extracted twice with ethyl acetate
  6. washthe combined organic phases were washed with brine
  7. dry with materialdried over anhydrous magnesium sulphate
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0d5b894a5b6e42a5a9b02d5fb7154a9c
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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