Potassium Carbonate → HCID 18368070, compound

HRID 379883Notes

Reaction equation

HRID 379883 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([C:24]2[N:25](C(OCC)=O)[C:26]3[C:31]([C:32]=2[NH:33][C:34](=[O:37])[CH2:35][CH3:36])=[CH:30][CH:29]=[C:28]([Cl:38])[CH:27]=3)=[O:23])[CH:17]=1)C(OC(C)(C)C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[C:1]([O:5][C:6]([NH:8][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([C:24]2[NH:25][C:26]3[C:31]([C:32]=2[NH:33][C:34](=[O:37])[CH2:35][CH3:36])=[CH:30][CH:29]=[C:28]([Cl:38])[CH:27]=3)=[O:23])[CH:17]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 18368020HCID 18368020, compound

Product 1

HCID 18368070HCID 18368070, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-[4-[N,N-bis(tert-butoxycarbonyl)amino]-2-pyridine-2-carbonyl]-6-chloro-1-ethoxycarbonyl-3-(propionylmino)indole (step 3, 240 mg, 0.391 mol) in ethanol (10 ml) was added a solution of potassium carbonate (260 mg, 3.91 mmol) in water (5 ml) at room temperature. After stirring for 8 h, the mixture was concentrated. The residue was diluted with ethyl acetate (100 ml) and washed with (50 ml×2), dried (Na2SO4). Removl of solvent gave an oily residue, which was purified by flash column chromatography eluting with ethyl acetate/hexane (1/3) to afford 118 mg (68%) of the title compound as an oil.

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe residue was diluted with ethyl acetate (100 ml)
  3. washwashed with (50 ml×2)
  4. dry with materialdried (Na2SO4)
  5. customRemovl of solvent gave an oily residue, which
  6. customwas purified by flash column chromatography
  7. washeluting with ethyl acetate/hexane (1/3)

Sources & evidence

ORD record
ord-3f0b014ed6bc40b6b6e234846ea53eb2
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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