tert-Butanol → HCID 22053388, compound

HRID 1829610Notes

Reaction equation

HRID 1829610 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](C(O)=O)[CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])=CC=1.CC[N:36]([CH2:39]C)CC.[CH3:41][C:42]([OH:45])([CH3:44])[CH3:43]>>[C:42]([O:45][C:39]([NH:36][C:6]1[CH:7]=[C:8]2[C:13](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)=[O:24])([CH3:44])([CH3:43])[CH3:41]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 71401918-nitroquinoline-6-carboxylic Acid

Product 1

HCID 22053388HCID 22053388, compoundYield 60%

Procedure

A mixture of 19 (4.82 g, 22.1 mmol), DPPA (6.99 g, 25.4 mmol) and Et3N (3.69 mL, 26.5 mmol) in anhydrous t-BuOH (60 mL) was heated at reflux under N2 for 8 h. The mixture was concentrated under reduced pressure, and the residue was partitioned between CH2Cl2 and 10% aqueous KHCO3. The organic phase was washed with 10% aqueous KHCO3, dried (Na2SO4) and concentrated under reduced pressure, then chromatographed on silica gel. Elution with CH2Cl2/EtOAc (17:3), followed by sequential crystallisation from MeOH/H2O and CH2Cl2/petroleum ether gave 20 (3.82 g, 60%): mp 134–135° C.; 1H NMR [(CD3)2SO]δ 10.09 (s, 1 H), 8.87 (dd, J=4.1, 1.5 Hz, 1 H), 8.47 (dd, J=8.5, 1.6 Hz, 1 H), 8.33 (d, J=1.9 Hz, 1 H), 8.25 (d, J=2.2 Hz, 1 H), 7.65 ,m(dd, J=2.2 Hz, 1 H), 7.65 (dd, J=8.5, 4.2 Hz, 1 H), 1.53 (s, 9 H). Anal. Calcd. for C14H15N3O4: C, 58.12; H, 5.23; N, 14.53. Found: C, 58.39; H, 5.21; N, 14.65%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 for 8 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between CH2Cl2 and 10% aqueous KHCO3
  5. washThe organic phase was washed with 10% aqueous KHCO3
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customchromatographed on silica gel
  9. washElution with CH2Cl2/EtOAc (17:3)
  10. customfollowed by sequential crystallisation from MeOH/H2O and CH2Cl2/petroleum ether

Sources & evidence

ORD record
ord-df23c6c6ea4e4e04a5a229d841600d30
Source dataset
uspto-grants-2006_06
Patent number
US07064117B2

Reaction notes

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