Acetic Acid → HCID 86649124, compound

HRID 1471041Notes

Reaction equation

HRID 1471041 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=3)[N:9]2[C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=2)=[CH:4][C:3]=1[NH:30][C:31]([C@@H:33]1[CH2:37][CH2:36][CH2:35][N:34]1[C:38](=[O:48])[C@@H:39]([NH:43][C:44](=[O:47])[O:45][CH3:46])[CH:40]([CH3:42])[CH3:41])=O.C(O)(=O)C>CCOC(C)=O.C(Cl)Cl>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([CH:10]2[N:9]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:27])[CH3:28])=[CH:22][CH:21]=3)[CH:8]([C:5]3[CH:6]=[CH:7][C:2]4[N:1]=[C:31]([C@@H:33]5[CH2:37][CH2:36][CH2:35][N:34]5[C:38](=[O:48])[C@@H:39]([NH:43][C:44](=[O:47])[O:45][CH3:46])[CH:40]([CH3:42])[CH3:41])[NH:30][C:3]=4[CH:4]=3)[CH2:12][CH2:11]2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86649122HCID 86649122, compound

Product 1

HCID 86649124HCID 86649124, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

The product from Example 191H (0.5 g, 0.696 mmole) was treated with acetic acid (5 mL, 87 mmole) and heated in an oil bath at 75° C. for 70 min. The reaction mixture was cooled to room temperature and concentrated in vacuo leaving an oily residue. The residue was dissolved in EtOAc (100 mL) washed with 10%0/NaHCO3 (20 mL) and 10% NaCl (20 mL), dried over anhydrous Na2SO4(s), filtered and solvent removed in vacuo leaving a brown foamy solid. The residue was dissolved in 10 mL CH2Cl2 and applied to a 12 g silica gel column. The column was eluted with a gradient of CH2Cl2/MeOH, 99/1 to 95/5 over 15 minutes and the product was isolated as a tan solid as a mixture of isomers (0.31 g). ESI(m/z)+: 702.3.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customleaving an oily residue
  4. washwashed with 10%0/NaHCO3 (20 mL) and 10% NaCl (20 mL)
  5. dry with materialdried over anhydrous Na2SO4(s)
  6. filtrationfiltered
  7. customsolvent removed in vacuo
  8. customleaving a brown foamy solid
  9. washThe column was eluted with a gradient of CH2Cl2/MeOH, 99/1 to 95/5 over 15 minutes
  10. customthe product was isolated as a tan solid as a mixture of isomers (0.31 g)

Sources & evidence

ORD record
ord-81650b5fef15429e8aeb32ee2849ded0
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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