Bicarbonate Ion → HCID 58522505, compound

HRID 718044Notes

Reaction equation

HRID 718044 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:19]([O-])=O)=[C:6]([CH:18]=1)[O:7][C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].O.C(=O)(O)[O-]>C(O)C.C(OCC)(=O)C>[NH2:19][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:18][C:6]=1[O:7][C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 962WaterHCID 59783605HCID 59783605, compound

Product 1

HCID 58522505HCID 58522505, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 50 (4.40 g, 14.30 mmol) and 5 nCl2.2H2O (16.13 g, 71.5 mmol) in ethanol (100 mL) was stirred at 80° C. for 3 h. Water and saturated bicarbonate solution (˜250 ml) was added (very effervescent). The reaction mixture was diluted with ethyl acetate and then Celite® was added and the mixture was stirred for 15 min then filtered. The filtrate was extracted with ethyl acetate twice, and the organic extract was dried over Na2SO4, filtered and concentrated. The crude was purified by flash chromatography, dry loaded with THF onto 80 g SiO2 and eluted with 0% to 50% ethyl acetate in hexanes to afford title compound 51 (2.10 g, 51%) as a beige solid. LRMS (ESI): (calc) 277.05. (found) 278.2 (MH)+. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.89 (dd, J=7.9, 1.7 Hz, 1H), 7.46 (ddd, J=7.9, 7.4, 1.8 Hz, 1H), 7.17 (td, J=7.6, 1.2 Hz, 1H), 6.97 (dd, J=8.3, 0.9 Hz, 1H), 6.94 (dd, J=8.4, 2.3 Hz, 1H), 6.79 (d, J=2.3 Hz, 1H), 6.73 (d, J=8.4 Hz, 1H), 4.05 (s, 2H), 3.87 (s, 3H).

Workup

  1. additionCelite® was added
  2. stirringthe mixture was stirred for 15 min
  3. filtrationthen filtered
  4. extractionThe filtrate was extracted with ethyl acetate twice
  5. extractionthe organic extract
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude was purified by flash chromatography
  10. dry with materialdry loaded with THF onto 80 g SiO2
  11. washeluted with 0% to 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6f874538d2084e7da2606fef40df6ea1
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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