Acetic Anhydride → HCID 136396916, compound

HRID 2110590Notes

Reaction equation

HRID 2110590 reaction equation
[NH2:1][C:2]1([CH2:31][CH2:32][CH2:33][CH3:34])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][C:16]=3[S:15](=[O:29])(=[O:28])[N:14]=2)[C:3]1=[O:30].C(N(CC)CC)C.[C:42](OC(=O)C)(=[O:44])[CH3:43].C([O-])([O-])=O.[K+].[K+]>ClCCl.CO.O>[CH2:31]([C:2]1([NH:1][C:42](=[O:44])[CH3:43])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][C:16]=3[S:15](=[O:29])(=[O:28])[N:14]=2)[C:3]1=[O:30])[CH2:32][CH2:33][CH3:34]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 136396942HCID 136396942, compound

Product 1

HCID 136396916HCID 136396916, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 26 (20 mg, 0.04 mmol) in dichloromethane (0.5 mL) was added triethylamine (17 μL, 0.12 mmol) and acetic anhydride (7 μL, 0.08 mmol) and the solution was stirred at room temperature for 16 hours. Solvent was removed in vacuo to yield bis-substituted material which is dissolved in methanol (2 mL) and solid K2CO3 (excess) was added and the solution stirred at room temperature for 1 hour. H2O (5 mL) was added and the solution extracted with ethyl acetate (3×5 mL). The combined extracts were washed with brine (1×5 mL), dried (Na2SO4), the drying agent filtered and the solvent removed in vacuo to give a crude residue which was purified by column chromatography on silica gel (3% methanol/chloroform) to give the title compound as a colorless solid. 1H NMR (d6-DMSO) δ 10.00 (s, 1H), 8.04, 8.01 (d, 1H), 7.57-7.33 (m, 6H), 3.02 (s, 3H), 1.91-1.79 (m, 1H), 1.82 (s, 3H), 1.72-1.62 (m, 1H), 1.31-1.13 (m, 2H), 0.89-0.63 (m, 2H), 0.72-0.63 (m, 3H). MS (ESI) m/z 547 (M+H+).

Workup

  1. customSolvent was removed in vacuo
  2. customto yield bis-substituted material which
  3. stirringthe solution stirred at room temperature for 1 hour
  4. extractionthe solution extracted with ethyl acetate (3×5 mL)
  5. washThe combined extracts were washed with brine (1×5 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationthe drying agent filtered
  8. customthe solvent removed in vacuo
  9. customto give a crude residue which
  10. customwas purified by column chromatography on silica gel (3% methanol/chloroform)

Sources & evidence

ORD record
ord-85ef94e1190f43a18e528923f91b43f2
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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