Acetic Anhydride → HCID 69438111, compound

HRID 404912Notes

Reaction equation

HRID 404912 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:17]=[C:16]([CH:18]([NH2:20])[CH3:19])[O:15][N:14]=3)=[CH:11][N:12]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:30](OC(=O)C)(=[O:32])[CH3:31]>ClCCl>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:17]=[C:16]([CH:18]([NH:20][C:30](=[O:32])[CH3:31])[CH3:19])[O:15][N:14]=3)=[CH:11][N:12]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69440052HCID 69440052, compound

Product 1

HCID 69438111HCID 69438111, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 53A (740 mg, 2.33 mmol) and triethylamine (975 μL, 7 mmol) in dichloromethane (15 mL) was added acetic anhydride (282 μL, 2.8 mmol) at ambient temperature. The reaction was stirred for 20 minutes, concentrated, and purified by flash chromatography on silica gel eluting with a solvent gradient from 30% to 80% ethyl acetate in hexanes to provide 796 mg (95%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.42 (d, J=6.99 Hz, 3H) 1.87 (s, 3H) 3.80 (s, 3H) 5.09 (m, 1H) 6.89 (s, 1H) 6.99-7.12 (m, 2H) 7.27-7.46 (m, 2H) 7.95 (s, 1H) 8.51 (d, J=8.09 Hz, 1H); MS (ESI) m/z 360.0 (M+H)+.

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography on silica gel eluting with a solvent gradient from 30% to 80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4341e03326ac49b7bf00639fb2e892ea
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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