tert-Butanol → HCID 58874048, compound

HRID 2405873Notes

Reaction equation

HRID 2405873 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

HCID 58874048HCID 58874048, compound

Procedure

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 1 N 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+).

Workup

  1. temperatureat reflux for 16 h
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with 1 N 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%)

Sources & evidence

ORD record
ord-7c82401eec0048d4b96021a2ac762465
Source dataset
uspto-grants-2014_08
Patent number
US08809327B2

Reaction notes

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