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

HRID 1689428노트

반응식

HRID 1689428 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([C:25]1[S:29][CH:28]=[C:27]([C:30]([N:32]2[CH2:37][C:36]3([CH2:42][CH2:41][N:40]([CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[C:46]([CH2:50][CH2:51][OH:52])[CH:45]=4)[CH2:39][CH2:38]3)[O:35][CH2:34][CH2:33]2)=[O:31])[CH:26]=1)[CH3:24].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>[CH2:23]([C:25]1[S:29][CH:28]=[C:27]([C:30]([N:32]2[CH2:37][C:36]3([CH2:42][CH2:41][N:40]([CH2:43][C:44]4[CH:45]=[C:46]([CH2:50][CH:51]=[O:52])[CH:47]=[CH:48][CH:49]=4)[CH2:39][CH2:38]3)[O:35][CH2:34][CH2:33]2)=[O:31])[CH:26]=1)[CH3:24]

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57989056(5-Ethylthiophen-3-yl)(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

생성물 1

HCID 579893622-(3-((4-(5-Ethylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Dess-Martin periodinane (0.232 g) was added to a stirred solution of (5-ethylthiophen-3-yl)(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (example 86, step a) (0.180 g) and trifluoroacetic acid (0.042 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, 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 0.17 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-adf59bf2f7e54d788fc90552fc1d1b21
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

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