Trifluoroacetic acid → 2-(5-((4-(2-Methylbenzo[d]thiazole-5-carbonyl)-1-oxa-4,9-diazaspiro[5,5]undecan-9-yl)methyl)thiophen-3-yl)acetaldehyde

HRID 1689325노트

반응식

HRID 1689325 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([CH2:31][N:32]2[CH2:54][CH2:53][C:35]3([O:40][CH2:39][CH2:38][N:37]([C:41]([C:43]4[CH:44]=[CH:45][C:46]5[S:50][C:49]([CH3:51])=[N:48][C:47]=5[CH:52]=4)=[O:42])[CH2:36]3)[CH2:34][CH2:33]2)[S:29][CH:30]=1.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>[CH3:51][C:49]1[S:50][C:46]2[CH:45]=[CH:44][C:43]([C:41]([N:37]3[CH2:36][C:35]4([CH2:53][CH2:54][N:32]([CH2:31][C:28]5[S:29][CH:30]=[C:26]([CH2:25][CH:24]=[O:23])[CH:27]=5)[CH2:33][CH2:34]4)[O:40][CH2:39][CH2:38]3)=[O:42])=[CH:52][C:47]=2[N:48]=1

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57989243(9-((4-(2-Hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylbenzo[d]thiazol-5-yl)methanone

생성물 1

HCID 579890032-(5-((4-(2-Methylbenzo[d]thiazole-5-carbonyl)-1-oxa-4,9-diazaspiro[5,5]undecan-9-yl)methyl)thiophen-3-yl)acetaldehyde

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Dess-Martin periodinane (0.27 g) was added to stirred solution of (9-((4-(2-hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylbenzo[d]thiazol-5-yl)methanone (example 49, step b) (0.20 g) and trifluoroacetic acid (0.033 mL) in DCM (5 mL). After 40 min, the reaction mixture was treated with aqueous saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (30 mL). The mixture was extracted twice with ethyl acetate, the combined organics were washed with saturated sodium bicarbonate solution, acetic acid (0.08 mL) was added, then the solution was dried over sodium sulphate, filtered, and evaporated in vacuo. Yield 0.2 g. Used directly in the next step.

후처리

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. washthe combined organics were washed with saturated sodium bicarbonate solution, acetic acid (0.08 mL)
  3. additionwas added
  4. dry with materialthe solution was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-1b37d24de5e74971a619e39395b9335d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

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