Trifluoroacetic acid → HCID 57554632, compound

HRID 1511906Notes

Reaction equation

HRID 1511906 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][C@@:11]1([NH:30]C(=O)OC(C)(C)C)[CH2:15][CH2:14][C@H:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:18][CH:17]=2)[CH2:12]1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(O)(C(F)(F)F)=O.CCCCCCC>ClCCl>[NH2:30][C@:11]1([CH2:10][CH2:9][P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:6][CH2:7][CH3:8])[CH2:15][CH2:14][C@H:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:18][CH:17]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8900HeptaneHCID 57554684HCID 57554684, compound

Product 1

HCID 57554632HCID 57554632, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (1R,3S)-1-(2-(diethoxyphosphoryl)ethyl)-3-(4-octylphenyl)cyclopentylcarbamate (0.2 g, 0.372 mmol) was dissolved in dichloromethane (1.860 ml) in a sealed vial to give a colorless solution. TFA (1.860 ml) was added and the reaction stirred for about 1 h. Solvents were removed under reduced pressure. Methylene chloride (25 mL) and saturated sodium bicarbonate (25 mL) were added and the layers separated and extracted with methylene chloride (2×10 mL). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated to a yellow oil. The oil was dissolve in ether (15 mL). 1 M HCl in dioxane (3 mL) was added. Solvents were removed under reduced pressure. The solid was redissolved in water and lyophilized. The resulting white/tan solid was suspended in ether and the resulting solid was collected by vacuum filtration and washed with ether then heptane to provide diethyl 2-((1R,3S)-1-amino-3-(4-octylphenyl)cyclopentyl)ethylphosphonate (0.0787 g, 0.180 mmol, 48.4% yield) as a white solid on drying under vacuum: LCMS (method a) Rt=3.46 min.; MS m/z: 438.48 (M+H)+.

Workup

  1. customto give a colorless solution
  2. customSolvents were removed under reduced pressure
  3. additionMethylene chloride (25 mL) and saturated sodium bicarbonate (25 mL) were added
  4. customthe layers separated
  5. extractionextracted with methylene chloride (2×10 mL)
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to a yellow oil
  10. dissolutionThe oil was dissolve in ether (15 mL)
  11. addition1 M HCl in dioxane (3 mL) was added
  12. customSolvents were removed under reduced pressure
  13. dissolutionThe solid was redissolved in water
  14. filtrationthe resulting solid was collected by vacuum filtration
  15. washwashed with ether

Sources & evidence

ORD record
ord-8793debc89b64d0d8bbf1ecd3968d8c1
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

Loading…