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

HRID 992906Notes

Reaction equation

HRID 992906 reaction equation
C([NH+](CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O-:37])=[O:36])([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](OC(C(F)(F)F)=O)=[C:47]([F:60])[C:46]=1[F:61]>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][C:45]2[C:50]([F:51])=[C:49]([F:52])[CH:48]=[C:47]([F:60])[C:46]=2[F:61])=[O:36])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 153342582,3,5,6-Tetrafluorophenyl trifluoroacetateHCID 1317236096-{[(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-c61d809eff54422b81eb36a9a84bd584
Source dataset
uspto-grants-2002_10
Patent number
US06472153B1

Reaction notes

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