Triethylamine → 2,3,5,6-Tetrafluorophenyl 6-{[(4-methoxyphenyl)diphenylmethyl]amino}hexanoate

HRID 1593533Notes

Reaction equation

HRID 1593533 reaction equation
C([NH+](CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([NH:29][CH:30]([CH2:34][CH2:35][CH2:36]C)C([O-])=O)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1.C(N(CC)CC)C.[CH:45]1[C:50]([F:51])=[C:49]([F:52])[C:48]([O:53][C:54]([C:56](F)(F)F)=[O:55])=[C:47]([F:60])[C:46]=1[F:61]>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([NH:29][CH2:30][CH2:34][CH2:35][CH2:36][CH2:56][C:54]([O:53][C:48]2[C:49]([F:52])=[C:50]([F:51])[CH:45]=[C:46]([F:61])[C:47]=2[F:60])=[O:55])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 153342582,3,5,6-Tetrafluorophenyl trifluoroacetateHCID 131726683([(4-Methoxyphenyl)diphenylmethyl]amino}hexanoic acid, triethylammonium salt

Product 1

HCID 184081682,3,5,6-Tetrafluorophenyl 6-{[(4-methoxyphenyl)diphenylmethyl]amino}hexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The acid 6 obtained as described above (2.2 g, 4.4 mmol) was dissolved in anhydrous CH2Cl2 and treated with 1 ml of triethylamine followed by 0.8 ml of 2,3,5,6-tetrafluorophenyltrifluoroacetate. After being kept at room temperature for 30 min, the reaction was concentrated to an oil (crude 7), which then was re-suspended in 20% ethyl acetate/80% hexane and applied to a silica gel column. Elution with 15% ethyl acetate/85% hexane and concentration of the pure product fractions afforded 2.0 g (82%) of the TFP ester (7) as a colorless, viscous oil.

Workup

  1. concentrationthe reaction was concentrated to an oil (crude 7), which
  2. washElution with 15% ethyl acetate/85% hexane and concentration of the pure product fractions

Sources & evidence

ORD record
ord-474c7fb7d18a4b00a575706a805ec96b
Source dataset
uspto-grants-2007_11
Patent number
US07297495B2

Reaction notes

Loading…