Water → 1-Carboxymethyl-1H-indole-3-carboxylic acid ethyl ester

HRID 1527205Notes

Reaction equation

HRID 1527205 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[CH:7]=1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:15][C:16]([OH:18])=[O:17])[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 682832491-tert-Butoxycarbonylmethyl-1H-indole-3-carboxylic acid ethyl ester

Product 1

HCID 190852681-Carboxymethyl-1H-indole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-tert-Butoxycarbonylmethyl-1H-indole-3-carboxylic acid ethyl ester (700 mg, 2.31 mmol) was dissolved in CH2Cl2 (12 mL), TFA (2.65 mL, 34.6 mmol) was added and the solution was stirred at RT over week end. CH2Cl2 and water were added, the layers were separated and the aqueous one re-extracted with CH2Cl2 (2×). The combined organic layers were dried with Na2SO4, filtered and concentrated to give the desired compound. TLC, Rf (EtOAc)=0.62; MS (LC/MS): 248.1 [M+H]+, 246.0 [M−H]−; tR (HPLC conditions a): 3.03 min.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous one re-extracted with CH2Cl2 (2×)
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1cc939b40ea045988e4d2cd32207abe9
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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