Trifluoroacetic acid → HCID 23000255, compound

HRID 398362Notes

Reaction equation

HRID 398362 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][NH:12]C(OC(C)(C)C)=O)[CH:9]=2)[NH:4][CH:3]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][NH2:12])[CH:9]=2)[NH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 54477116HCID 54477116, compound

Product 1

HCID 23000255HCID 23000255, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-5-(t-butoxycarbonylaminomethyl)-indole (2.62 g, 9.33 mmol) in CH2Cl2 (25 mL), cooled to 0° C. was added trifluoroacetic acid (10 mL). After 1 h the reaction was basified with aqueous NaOH (1 N) to pH=10, extracted with CH2Cl2 (3×) and then with CH2Cl2:MeOH (3:1). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo. Purification of the resulting orange residue by flash chromatography (30×150 mm column; gradient elution with MeOH:CH2Cl2:CH2Cl2 saturated with NH3, 4:66:30 to 10:60:30 500 mL each) afforded the title compound as a yellow oil:

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the resulting orange residue
  6. washby flash chromatography (30×150 mm column; gradient elution with MeOH:CH2Cl2:CH2Cl2 saturated with NH3, 4:66:30 to 10:60:30 500 mL each)

Sources & evidence

ORD record
ord-1058f7f25360458e940df0656da6fafa
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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