Acetic Anhydride → HCID 10278068, compound

HRID 2306089Notes

Reaction equation

HRID 2306089 reaction equation
[CH2:1]([O:8][NH:9][C@@H:10]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)[CH2:11][N:12]1[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[NH:14][C:13]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](OC(=O)C)(=[O:32])C>C(O)=O>[CH2:1]([O:8][N:9]([C@H:10]([CH2:11][N:12]1[C:16](=[O:17])[C:15]([CH3:18])([CH3:19])[NH:14][C:13]1=[O:20])[CH2:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([Br:29])=[CH:27][CH:28]=1)[CH:30]=[O:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10276449HCID 10276449, compound

Product 1

HCID 10278068HCID 10278068, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of Example 3H (57.7 g) in formic acid (200 mL) was treated with a mixture of acetic anhydride (35 mL) in formic acid (35 mL) over 10 minutes, stirred for 10 minutes, and concentrated. The concentrate was dissolved in ethyl acetate (500 mL), washed sequentially with 1:1/water:brine, saturated NaHCO3, and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was dissolved in warm (60° C.) toluene, cooled, and filtered. The solid was washed with 1:1/toluene:heptane then dried under vacuum (100 mm Hg) at 50° C. with a nitrogen bleed to provide 51.7 g of the desired product. 1H NMR (300 MHz, DMSO-d6) δ8.42 (br s, 0.5H), 8.38 (br s, 0.5H), 8.32 (br s, 0.5H), 8.10 (br s, 0.5H), 7.4 (m, 7H), 6.95 (m, 2H), 5.00 (m, 1H), 4.91 (m, 1H) 4.80 (m, 0.5H), 4.55 (m, 0.5H), 4.28(m, 1H), 4.17 (m, 1H), 3.88 (dd, 1H, J=9, 14 Hz), 3.60 (m, 1H), 1.25 (s, 3H), 1.22 (s, 3H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in ethyl acetate (500 mL)
  3. washwashed sequentially with 1:1/water
  4. dry with materialbrine, saturated NaHCO3, and brine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe concentrate was dissolved
  8. temperaturecooled
  9. filtrationfiltered
  10. washThe solid was washed with 1:1/toluene
  11. dry with materialheptane then dried under vacuum (100 mm Hg) at 50° C. with a nitrogen

Sources & evidence

ORD record
ord-c6fe715b2ec7454d90fc788e7e4bcdbe
Source dataset
uspto-grants-2002_08
Patent number
US06441189B1

Reaction notes

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