Trifluoroacetic acid → Indoline-3(R,S)-carboxylic acid (N-methyl)amide

HRID 863313Notes

Reaction equation

HRID 863313 reaction equation
FC(F)(F)C(O)=O.[CH3:8][NH:9][C:10]([CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14](C(OC(C)(C)C)=O)[CH2:13]1)=[O:11]>C(Cl)Cl>[CH3:8][NH:9][C:10]([CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 766348041-(Tert-butoxycarbonyl)indolin-3(R,S)-carboxylic acid (N-methyl)amide

Product 1

HCID 76443689Indoline-3(R,S)-carboxylic acid (N-methyl)amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3 ml of a 25% solution of trifluoroacetic acid in methylene chloride are added to a solution of 216 mg of 1-(tert-butoxycarbonyl)indoline-3(R,S)-carboxylic acid (N-methyl)amide in 1 ml of methylene chloride at 0° C., while stirring. After 90 min, the mixture is allowed to warm to room temperature and stirring is continued for 2 h. Concentration of the mixture and purification of the crude product over 50 g of silica gel (mobile phase K) gives the title compound: Rf (P)=0.52.

Workup

  1. stirringstirring
  2. waitis continued for 2 h
  3. customConcentration of the mixture and purification of the crude product over 50 g of silica gel (mobile phase K)

Sources & evidence

ORD record
ord-55df9619015a46a195a4a423f8ce2113
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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