Trifluoroacetic acid → 2-(3-((4-(Benzo[b]thiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)-2-fluorophenyl)acetaldehyde

HRID 471181노트

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HRID 471181 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[S:23]1[C:27]([C:28]([N:30]2[CH2:35][C:34]3([CH2:40][CH2:39][N:38]([CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][CH2:49][OH:50])[C:43]=4[F:51])[CH2:37][CH2:36]3)[O:33][CH2:32][CH2:31]2)=[O:29])=[CH:26][C:25]2[CH:52]=[CH:53][CH:54]=[CH:55][C:24]1=2.FC(F)(F)C(O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[S:23]1[C:27]([C:28]([N:30]2[CH2:35][C:34]3([CH2:40][CH2:39][N:38]([CH2:41][C:42]4[C:43]([F:51])=[C:44]([CH2:48][CH:49]=[O:50])[CH:45]=[CH:46][CH:47]=4)[CH2:37][CH2:36]3)[O:33][CH2:32][CH2:31]2)=[O:29])=[CH:26][C:25]2[CH:52]=[CH:53][CH:54]=[CH:55][C:24]1=2

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57989186Benzo[b]thiophen-2-yl(9-(2-fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

생성물 1

HCID 579893902-(3-((4-(Benzo[b]thiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)-2-fluorophenyl)acetaldehyde

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Dess-Martin periodinane (0.282 g) was added to a stirred solution of benzo[b]thiophen-2-yl(9-(2-fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (example 79, step b) (0.240 g) and trifluoroacetic acid (0.059 mL) in DCM (5 mL). After 1 h, ethyl acetate (30 mL) was added followed by a mixture of saturated sodium thiosulphate solution (5 mL) and saturated sodium bicarbonate solution (5 mL). The reaction mixture was shaken well and separated. The ethyl acetate solution was washed with saturated sodium bicarbonate solution, water and brine. Acetic acid (0.08 mL) was added, then the solution was dried over sodium sulphate, filtered and evaporated in vacuo (bath temperature ˜30° C.) to give the subtitled compound as a gum. Yield 0.24 g. Used directly.

후처리

  1. customseparated
  2. washThe ethyl acetate solution was washed with saturated sodium bicarbonate solution, water and brine
  3. additionAcetic acid (0.08 mL) was added
  4. dry with materialthe solution was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo (bath temperature ˜30° C.)

출처 및 근거

ORD 기록
ord-c28d3d3dc83242ddaafd918aa4a12a15
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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