tert-Butanol → HCID 58874048、化合物

HRID 57161ノート

反応式

HRID 57161 の反応式
[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1C(O)=O.C([N:16]([CH2:20]C)C(C)C)(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>>[C:39]([O:43][C:20](=[O:29])[NH:16][C:2]1[S:1][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1)([CH3:42])([CH3:41])[CH3:40]

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 7162095Thieno(2,3-b)pyridine-2-carboxylic acid

生成物 1

HCID 58874048HCID 58874048、化合物

実験手順

A solution of compound 147-C (0.36 g, 2.00 mmol), N,N-diisopropylethylamine (0.385 mL, 2.21 mmol) and diphenyl phosphoryl azide (0.536 mL, 2.41 mmol) in t-butanol (3.6 mL) was heated at reflux for 16 h. The solvent was evaporated in vacuo, the residue dissolved in dichloromethane, washed with 1N NaOH, brine, dried with Na2SO4, filtered, and evaporated to afford a residue. Flash column chromatography (SiO2) eluting with dichloromethane afforded compound 147-D as a white solid (0.25 g, 50%). 1H-NMR (CDCl3): δ 1.55 (s, 9H), 6.60 (s, 1H), 7.20 (dd, 1H), 7.80 (d, 1H), 8.40 (d, 1H); MS: m/z 251.2 (MH+).

後処理

  1. temperatureat reflux for 16 h
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with 1N NaOH, brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a residue
  9. washFlash column chromatography (SiO2) eluting with dichloromethane afforded compound 147-D as a white solid (0.25 g, 50%)

出典と根拠

ORDレコード
ord-cb8c568bd5b14130b231a93eb0aa4194
出典データセット
uspto-grants-2016_09
特許番号
US09434711B2

反応ノート

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