Acetyl chloride → HCID 21834611, compound

HRID 1292672Notes

Reaction equation

HRID 1292672 reaction equation
[C:1]([C:3]1[CH:35]=[CH:34][C:6]([CH2:7][N:8]2[C:12]([CH2:13][C:14]([NH:16][CH:17]([CH2:32][NH2:33])[C:18]([NH:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)=[O:19])=[O:15])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.[C:43](Cl)(=[O:45])[CH3:44]>C(Cl)(Cl)Cl.CN(C=O)C.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]([CH2:13][C:14]([NH:16][CH:17]([CH2:32][NH:33][C:43](=[O:45])[CH3:44])[C:18]([NH:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)=[O:19])=[O:15])=[CH:11][N:10]=[CH:9]2)=[CH:34][CH:35]=1)#[N:2]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 54408887HCID 54408887, compound

Product 1

HCID 21834611HCID 21834611, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Example 32 (37.3 mg, 69.1 mmol), and triethylamine (52 μl, 345 mmol) in CHCl3 (0.85 ml) and DMF (0.5 ml) at 0° C., was added acetyl chloride (5.0 μl 69.1 mmol). The reaction was vortexed and allowed to stand at room temperature for 18 hrs. The reaction was diluted with EtOAc and the organic layer washed with sat. aq NaHCO3, brine and dried (Na2SO4). The solvent evaporated in vacuo and the residue was purified by preparative HPLC (C-18; 95:5 to 5:95 Water:CH3CN containing 0.1% trifluoroacetic acid; gradient elution), to afford the title compound as a white solid.

Workup

  1. washthe organic layer washed with sat. aq NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent evaporated in vacuo
  4. customthe residue was purified by preparative HPLC (C-18; 95:5 to 5:95 Water:CH3CN containing 0.1% trifluoroacetic acid; gradient elution)

Sources & evidence

ORD record
ord-4806440dfd8b4ec0bc278a91770f62a3
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

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