Trifluoroacetic acid → HCID 67340836, compound

HRID 1670117Notes

Reaction equation

HRID 1670117 reaction equation
C([O:5][C:6](=[O:43])[C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:21]=2[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:10]=[C:9]([Br:42])[CH:8]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Br:42][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:21]=2[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:10]=1)[C:6]([OH:43])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673397313-Bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic Acid tert-butyl Ester

Product 1

HCID 67340836HCID 67340836, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic acid tert-butyl ester (2.3 g, 3.46 mmol) in dichloromethane (25 mL) was added trifluoroacetic acid (10 mL) at room temperature. The resulting light brown solution was stirred for 4 h. Then, the dichloromethane and excess TFA was removed under reduced pressure and the residue was dissolved in toluene and again removed under reduced pressure to remove all TFA to obtain 3-bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic acid (2.1 g, 100%) as a light brown oil.

Workup

  1. customThen, the dichloromethane and excess TFA was removed under reduced pressure
  2. dissolutionthe residue was dissolved in toluene
  3. customagain removed under reduced pressure
  4. customto remove all TFA

Sources & evidence

ORD record
ord-bb146cba12544b328280126572fd5488
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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