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

HRID 471000
ノート
印刷プレビュー

反応式

HRID 471000 の反応式
C(O)(C(F)(F)F)=O.[OH:8][CH2:9][CH2:10][C:11]1[CH:36]=[CH:35][C:14]([CH2:15][N:16]2[CH2:34][CH2:33][C:19]3([O:24][CH2:23][CH2:22][N:21]([C:25]([C:27]4[N:28]=[C:29]([CH3:32])[S:30][CH:31]=4)=[O:26])[CH2:20]3)[CH2:18][CH2:17]2)=[CH:13][CH:12]=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>[CH3:32][C:29]1[S:30][CH:31]=[C:27]([C:25]([N:21]2[CH2:20][C:19]3([CH2:33][CH2:34][N:16]([CH2:15][C:14]4[CH:13]=[CH:12][C:11]([CH2:10][CH:9]=[O:8])=[CH:36][CH:35]=4)[CH2:17][CH2:18]3)[O:24][CH2:23][CH2:22]2)=[O:26])[N:28]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57988939(9-(4-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

生成物 1

HCID 57989122
2-(4-((4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

TFA (0.030 mL) was added to a solution of (9-(4-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 16, step b) (0.16 g) in DCM (5 mL) at 0° C. and the resulting mixture stirred for 5 min. Dess-Martin periodinane (0.245 g) was added and the mixture allowed to warm to room temperature and stirred for 45 min. A mixture of saturated sodium thiosulphate solution (5 mL), saturated sodium bicabonate solution (5 mL) and ethyl acetate (20 mL) was then added and the resulting 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. AcOH (0.1 mL) was then added and the mixture dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a clear oil which was used immediately. Yield 0.16 g.

後処理

  1. stirringstirred for 45 min
  2. additionwas then added
  3. stirringthe resulting mixture stirred for 10 min
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate (20 mL)
  6. washThe combined organic solutions were washed with brine
  7. additionAcOH (0.1 mL) was then added
  8. dry with materialthe mixture dried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated in vacuo

出典と根拠

ORDレコード
ord-547a428bc1d54503bae3ef8a8ae1f72c
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08629271B2

反応ノート

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