Trifluoroacetic acid → HCID 23557275, compound

HRID 1246255Notes

Reaction equation

HRID 1246255 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([C:18]([O:20]C(C)(C)C)=[O:19])[C:11]([O:13]C(C)(C)C)=[O:12])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([C:11]([OH:13])=[O:12])[C:18]([OH:20])=[O:19])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23557313HCID 23557313, compound

Product 1

HCID 23557275HCID 23557275, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of triester 61 (500 mg, 1.395 mmol) in CH2Cl2 (20 mL) was added TFA (2.0 mL) and the reaction mixture stirred overnight. Volatile components were evaporated under vacuum, and the residue repeatedly dissolved in CH2Cl2 and evaporated to remove all traces of TFA. A solid 62 (327 mg, 1.33 mmol) was obtained and used directly in the next step without further purification. 1H-NMR (400 MHz, DMSO-d6) δ 12.62 (br s, 2H), 4.03 (q, 2H), 3.16 (t, 1H), 2.25 (t, 2H), 1.67 (m, 2H), 1.49 (m, 2H), 1.25 (m, 4H), 1.16 (t, 3H).

Workup

  1. customVolatile components were evaporated under vacuum
  2. dissolutionthe residue repeatedly dissolved in CH2Cl2
  3. customevaporated
  4. customto remove all traces of TFA

Sources & evidence

ORD record
ord-94e6bf2cf1e6448fa9059eb91e1e145f
Source dataset
uspto-grants-2006_10
Patent number
US07126001B2

Reaction notes

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