Hydrochloric Acid → HCID 18367802, compound

HRID 379909Notes

Reaction equation

HRID 379909 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([C:16]([C:18]2[N:19](C(OCC)=O)[C:20]3[C:25]([C:26]=2[NH:27][C:28](=[O:31])[CH2:29][CH3:30])=[CH:24][CH:23]=[C:22]([Cl:32])[CH:21]=3)=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C(O)C.C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[C:11]([C:16]([C:18]2[NH:19][C:20]3[C:25]([C:26]=2[NH:27][C:28](=[O:31])[CH2:29][CH3:30])=[CH:24][CH:23]=[C:22]([Cl:32])[CH:21]=3)=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18367820HCID 18367820, compound

Product 1

HCID 18367802HCID 18367802, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 2-[3-(tert-butyldimethylsilyloxymethyl)pyridine-2-carbonyl]-6-chloro-1-ethoxycarbonyl-3-(propionylamino)indole (step 4, 890 mg, 1.64 mmol) in ethanol-THF (2:1, 30 ml) was added 2N aqueous NaOH (5 ml) at 0° C. After stirring for 1.5 h, the mixture was neutralized with 2N aqueous HCl (5 ml). The mixture was concentrated and the residue was diluted with ethyl acetate (200 ml). The organic solution was washed with water (50 ml×2), dried (MgSO4), and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1:15) to afford 663 mg (82%) of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate (200 ml)
  3. washThe organic solution was washed with water (50 ml×2)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography
  7. washeluting with ethyl acetate/hexane (1:15)

Sources & evidence

ORD record
ord-88773075811a46fa89726d36b7e18fa6
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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