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

HRID 471007ノート

反応式

HRID 471007 の反応式
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

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 46240300HCID 46240300、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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 bicabonate 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.

後処理

  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

出典と根拠

ORDレコード
ord-4c7ef0d045514418a1bdb94bb0cd1090
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

読み込み中…