Trifluoroacetic acid → HCID 59741474, compound

HRID 1669627Notes

Reaction equation

HRID 1669627 reaction equation
C(OC([NH:8][CH:9]([C:14]1([C:18]2[CH:30]=[CH:29][C:21]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][CH:19]=2)[CH2:17][CH2:16][CH2:15]1)[CH2:10][CH:11]([CH3:13])[CH3:12])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH:9]([C:14]1([C:18]2[CH:19]=[CH:20][C:21]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:29][CH:30]=2)[CH2:15][CH2:16][CH2:17]1)[CH2:10][CH:11]([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59741469HCID 59741469, compound

Product 1

HCID 59741474HCID 59741474, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 69 (0.25 g, 0.0005 mole) in 20 mL of 1:1 mixture of DCM and trifluoroacetic acid (TFA) was stirred at room temperature for 8 hours. The progress of the reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure. The residue was diluted with DCM (50 mL), washed with brine (25 mL), dried over sodium sulfate (Na2SO4) and evaporated. The residue was purified by 0-100% gradient of ethyl acetate and hexane as eluent to give the pure amine 70 as colorless oil in 85% (0.13 g) yield. 1H NMR (400 MHz, CDCl3): δ 0.85 (3H, broad s); 0.83 (3H, broad s); 1.25 (3H, t, J=4.5 Hz); 1.59 (1H, m); 1.85 (2H, m); 1.93 (2H, m); 2.20 (2H, m); 2.42 (2H, m); 2.68 (2H, m); 3.21 (1H, m); 4.08 (2H, q, J=4.5 Hz); 5.09 (2H, s); (6.81 (2H, broad d); 7.13 (2H, broad d).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with DCM (50 mL)
  3. washwashed with brine (25 mL)
  4. dry with materialdried over sodium sulfate (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by 0-100% gradient of ethyl acetate and hexane as eluent

Sources & evidence

ORD record
ord-15a13e6a924b4551899b1ea7a90d0d89
Source dataset
uspto-grants-2011_08
Patent number
US07989500B2

Reaction notes

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