Trifluoroacetic acid → HCID 9883924, compound

HRID 989627Notes

Reaction equation

HRID 989627 reaction equation
C([O:5][P:6]([CH2:17][CH:18]([CH2:26][CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])[C:19]([O:21]C(C)(C)C)=[O:20])([CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:10]([NH:9][CH2:8][P:6]([CH2:17][CH:18]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:19]([OH:21])=[O:20])([OH:7])=[O:5])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10951162HCID 10951162, compound

Product 1

HCID 9883924HCID 9883924, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of di-tert-butyl 2-[((tert-butoxy)-{[benzylamino]methyl}phosphoryl)methyl]pentane-1,5-dioate (0.498 g, 1.0 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (5 mL) at 0° C., and the mixture was stirred at room temperature for eighteen hours. The solvent was removed under reduced pressure. The residual oil was taken up with dichloromethane (10 mL) and concentrated. This process was repeated three times to remove trifluoroacetic acid completely. The resulting oil was crystallized from methanol to give 0.174 g of white solid (53% yield): 1H NMR (D2O) δ 1.40-1.48 (m, 27H), 1.7-2.1 (m, 4H), 2.2-2.4 (m, 3H), 2.6-3.0 (m, 3H), 3.8-4.0 (m, 2H), 7.2-7.4 (m, 5H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. concentrationconcentrated
  3. customto remove trifluoroacetic acid completely
  4. customThe resulting oil was crystallized from methanol

Sources & evidence

ORD record
ord-33bf5ce955c646929b04a99691c95a53
Source dataset
uspto-grants-2002_10
Patent number
US06458775B1

Reaction notes

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