Trifluoroacetic acid → HCID 18926538, compound

HRID 1600187Notes

Reaction equation

HRID 1600187 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]([CH2:12][CH2:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([CH2:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[CH:20][CH:21]=2)[C:16]([CH2:32][C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)=[CH:15]1)=[O:11]>ClCCl>[C:25]([CH2:24][CH2:23][C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[N:14]([CH2:13][CH2:12][C:10]([O:9][CH3:8])=[O:11])[CH:15]=[C:16]2[CH2:32][C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18926564HCID 18926564, compound

Product 1

HCID 18926538HCID 18926538, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (15 ml) was added to a stirred solution of t-butyl 1-(2-methoxycarbonylethyl)-3-(3-pyridylmethyl)-1H-indole-5-propanoate (7.60 g) in dry dichloromethane (100 ml) at room temperature, and stirringwas continued for 18 hours. The solution was evaporated and the residue wasazeotroped with toluene and then dissolved in ethyl acetate. Saturated sodium bicarbonate solution was added slowly with shaking until the pH of the aqueous layer was 4-5. The organic layer was then separated, washed with water and dried (MgSO4). The solvent was evaporated and the residue was triturated with ether to give the title compound (5.70 g), m.p. 108°-110° C. Found: C,68.80; H,6.16; N,7.57%. C21 H22N2O4 requires: C,68.83; H,6.05; N,7.65%.

Workup

  1. customThe solution was evaporated
  2. dissolutiondissolved in ethyl acetate
  3. additionSaturated sodium bicarbonate solution was added slowly
  4. customThe organic layer was then separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated
  8. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-b8e6ed3465804b15a6080513d1e86e59
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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