Acetic Anhydride → HCID 22709922, compound

HRID 352812Notes

Reaction equation

HRID 352812 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=3)(=[O:16])=[O:15])[CH2:10][CH:9]1[C:27](=[O:38])[NH:28][CH2:29][C:30]1[O:31][CH:32]=[C:33]([OH:37])[C:34](=[O:36])[CH:35]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:39](OC(=O)C)(=[O:41])[CH3:40].C(N(CC)CC)C>C(#N)C>[C:39]([O:37][C:33]1[C:34](=[O:36])[CH:35]=[C:30]([CH2:29][NH:28][C:27]([CH:9]2[CH2:10][N:11]([S:14]([C:17]3[NH:18][C:19]4[C:24]([CH:25]=3)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=4)(=[O:16])=[O:15])[CH2:12][CH2:13][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:38])[O:31][CH:32]=1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22710504HCID 22710504, compound

Product 1

HCID 22709922HCID 22709922, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In acetonitrile (10 ml) was dissolved 1-(tert-butoxycarbonyl)-4-[(5-chloroindol-2-yl)sulfonyl]-2-[N-[(5-hydroxy-4-oxo-4H-pyran-2-yl)methyl]carbamoyl]piperazine (411 mg), followed by the addition of acetic anhydride (0.075 ml) and triethylamine (0.11 ml). The resulting mixture was stirred at room temperature for 15 minutes. The reaction mixture was concentrated under reduced pressure. Methylene chloride was added to the residue. The resulting mixture was washed successively with 0.2N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and saturated aqueous NaCl solution. The organic layer was then dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (methylene chloride:methanol=50:5), whereby the title compound (256 mg) was obtained as a colorless foam.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionMethylene chloride was added to the residue
  3. washThe resulting mixture was washed successively with 0.2N hydrochloric acid
  4. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  5. customThe residue obtained
  6. distillationby distilling off the solvent under reduced pressure
  7. customwas purified by chromatography on a silica gel column (methylene chloride:methanol=50:5), whereby the title compound (256 mg)
  8. customwas obtained as a colorless foam

Sources & evidence

ORD record
ord-178677242164498da872d3c64267d2a0
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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