Trifluoroacetic acid → 2-(2-(2-((2,6-Dichlorophenyl)amino)phenyl)acetyloxy)ethanamine

HRID 514972Notes

Reaction equation

HRID 514972 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12](=[O:29])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][O:11][C:12](=[O:29])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118302985[2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid 2-tert-butoxycarbonylamino-ethyl ester

Product 1

HCID 769604762-(2-(2-((2,6-Dichlorophenyl)amino)phenyl)acetyloxy)ethanamineYield 24.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid 2-tert-butoxycarbonylamino-ethyl ester 4 (5.3 g, 0.01 mol) in DCM (50 mL) was added TFA (5.3 mL) at 0° C. The resulting mixture was stirred at room temperature for 16 h. Reaction was monitored by TLC. After completion, reaction mixture was concentrated under reduced pressure. The residue was neutralized with aq sodium bicarbonate and extracted with DCM (2×50 mL). Combined organic layer was dried over anhy Na2SO4 and evaporated under reduced pressure. Crude compound was purified by silica gel column chromatography using methanol and DCM (5:95) to get 1.0 g (24.4% Yield) Compound-5 as a brown solid; Mass: 339.0 (M++H).

Workup

  1. customReaction
  2. customAfter completion, reaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. extractionextracted with DCM (2×50 mL)
  5. dry with materialCombined organic layer was dried over anhy Na2SO4
  6. customevaporated under reduced pressure
  7. customCrude compound was purified by silica gel column chromatography
  8. customto get 1.0 g (24.4% Yield)

Sources & evidence

ORD record
ord-361fb4c794a94a359e3ca89f0c452d6c
Source dataset
uspto-grants-2015_08
Patent number
US09108942B1

Reaction notes

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