Trifluoroacetic acid → 2-(2,6-Difluoro-3-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

HRID 471080노트

반응식

HRID 471080 반응식
C(O)(C(F)(F)F)=O.[F:8][C:9]1[C:36]([CH2:37][CH2:38][OH:39])=[C:35]([F:40])[CH:34]=[CH:33][C:10]=1[CH2:11][N:12]1[CH2:32][CH2:31][C:15]2([O:20][CH2:19][CH2:18][N:17]([C:21]([C:23]3[N:24]=[C:25]([CH:28]([CH3:30])[CH3:29])[S:26][CH:27]=3)=[O:22])[CH2:16]2)[CH2:14][CH2:13]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[C:10]([CH2:11][N:12]2[CH2:32][CH2:31][C:15]3([O:20][CH2:19][CH2:18][N:17]([C:21]([C:23]4[N:24]=[C:25]([CH:28]([CH3:30])[CH3:29])[S:26][CH:27]=4)=[O:22])[CH2:16]3)[CH2:14][CH2:13]2)=[CH:33][CH:34]=[C:35]([F:40])[C:36]=1[CH2:37][CH:38]=[O:39]

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57988951(9-(2,4-Difluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

생성물 1

HCID 579893052-(2,6-Difluoro-3-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

TFA (0.11 mL) was added to a solution of (9-(2,4-difluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 45, step c) (0.7 g) in DCM (5 mL) at 0° C. and the resulting mixture stirred for 5 min. Dess-Martin periodinane (0.93 g) was then added and the mixture stirred at RT for 45 min. Saturated sodium thiosulphate solution (5 mL), saturated sodium bicabonate solution (5 mL) and ethyl acetate (20 mL) was then added and the mixture stirred for 10 min. The aqueous layer was separated and extracted with ethyl acetate (20 mL). The combined organics were washed with brine, acidified with a few drops of acetic acid, the mixture dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a clear gum. Yield 0.64 g.

후처리

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

출처 및 근거

ORD 기록
ord-74c74ad54e674937a8c57fcb87ddcb1d
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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