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 1689325ノート

反応式

HRID 1689325 の反応式
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

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1b37d24de5e74971a619e39395b9335d
出典データセット
uspto-grants-2012_04
特許番号
US08148373B2

反応ノート

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