Acetyl chloride → HCID 136397069, compound

HRID 2110575Notes

Reaction equation

HRID 2110575 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:15][O:16][CH3:17])([CH2:12][CH2:13][CH3:14])[C:4](=[O:18])[C:3]=1[C:19]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][C:22]=2[S:21](=[O:35])(=[O:34])[N:20]=1.C(N(CC)C(C)C)(C)C.[C:45](Cl)(=[O:47])[CH3:46]>O1CCCC1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:15]([O:16][CH3:17])[C:45](=[O:47])[CH3:46])([CH2:12][CH2:13][CH3:14])[C:4](=[O:18])[C:3]=1[C:19]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][C:22]=2[S:21](=[O:35])(=[O:34])[N:20]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 136383506HCID 136383506, compound

Product 1

HCID 136397069HCID 136397069, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 9 (15 mg, 0.029 mmol) in tetrahydrofuran (200 μL) was added N,N-diisopropylethylamine (11 μL, 0.062 mmol) and acetyl chloride (5 μL, 0.070 mmol) and stirring was continued overnight. The solution was concentrated and taken up in H2O (1 mL) and 1N NaOH (0.5 mL). This solution was stirred at room temperature for 2 hours and 1N HCl was added slowly until the solution became acidic. This aqueous solution was extracted with ethyl acetate (3×2 mL), the organic extracts combined, dried over Na2SO4, the drying agent filtered off, the solvent removed in vacuo, and the crude product was purified by column chromatography on silica gel (5% methanol/chloroform) to give the title compound as a colorless solid: 1H NMR (d6-DMSO) δ 13.81 (s, 1H), 10.18 (s, 1H), 8.10, 8.07 (d, 1H), 7.71-7.45 (m, 7H), 4.07 (s, 3H), 3.06 (s, 3H), 2.03 (br s, 3H), 1.30-1.05 (br s, 1H), 1.24 (br s, 2H), 0.75-0.50 (br s, 1H), 0.74-0.65 (t, 3H); MS (ESI) m/z 563 (M+H+).

Workup

  1. concentrationThe solution was concentrated
  2. stirringThis solution was stirred at room temperature for 2 hours
  3. addition1N HCl was added slowly until the solution
  4. extractionThis aqueous solution was extracted with ethyl acetate (3×2 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationthe drying agent filtered off
  7. customthe solvent removed in vacuo
  8. customthe crude product was purified by column chromatography on silica gel (5% methanol/chloroform)

Sources & evidence

ORD record
ord-97d602452b3e407cbb5ae43a621e9d8b
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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