Trifluoroacetic acid → 3-Fluoro-5-[[4-[(2-methyl-4-thiazolyl)carbonyl]-1-oxa-4,9-diazaspiro[5.5]undec-9-yl]methyl]benzeneacetaldehyde

HRID 1689238노트

반응식

HRID 1689238 반응식
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:32]=[C:33]([CH2:35][CH2:36][OH:37])[CH:34]=1)[CH2:12][N:13]1[CH2:31][CH2:30][C:16]2([O:21][CH2:20][CH2:19][N:18]([C:22]([C:24]3[N:25]=[C:26]([CH3:29])[S:27][CH:28]=3)=[O:23])[CH2:17]2)[CH2:15][CH2:14]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[F:8][C:9]1[CH:34]=[C:33]([CH2:35][CH:36]=[O:37])[CH:32]=[C:11]([CH2:12][N:13]2[CH2:31][CH2:30][C:16]3([O:21][CH2:20][CH2:19][N:18]([C:22]([C:24]4[N:25]=[C:26]([CH3:29])[S:27][CH:28]=4)=[O:23])[CH2:17]3)[CH2:15][CH2:14]2)[CH:10]=1

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 46240300HCID 46240300, 화합물

생성물 1

HCID 579893163-Fluoro-5-[[4-[(2-methyl-4-thiazolyl)carbonyl]-1-oxa-4,9-diazaspiro[5.5]undec-9-yl]methyl]benzeneacetaldehyde

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

TFA (0.08 mL) was added to a solution of (9-(3-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 19, step b) (0.46 g) in DCM (5 mL) at 0° C. and the resulting mixture stirred for 5 min. Dess-Martin periodinane (0.68 g) was then added and the mixture stirred at RT for 45 min. Saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (20 mL) were then added and the mixture stirred for 10 min. The aqueous phase was separated and extracted with ethyl acetate (20 mL). The combined organic solutions were washed with brine, acidified with acetic acid (0.1 mL), dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a yellow gum. Yield 0.4 g.

후처리

  1. stirringthe mixture stirred at RT for 45 min
  2. stirringthe mixture stirred for 10 min
  3. customThe aqueous phase was separated
  4. extractionextracted with ethyl acetate (20 mL)
  5. washThe combined organic solutions were washed with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-60324889b3b64bfd8bdfe72816c2da47
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

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