Water → HCID 57554773, compound

HRID 1511904Notes

Reaction equation

HRID 1511904 reaction equation
C([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]CC)=[O:5])C.Br[Si](C)(C)C.O.CCCCC>ClCCl>[NH2:30][C@:11]1([CH2:10][CH2:9][P:4](=[O:3])([OH:6])[OH:5])[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

6

Reactant 4

HCID 962WaterHCID 8003PentaneHCID 76113BromotrimethylsilaneHCID 57554684HCID 57554684, compound

Product 1

HCID 57554773HCID 57554773, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (1R,3S)-1-(2-(diethoxyphosphoryl)ethyl)-3-(4-octylphenyl)cyclopentylcarbamate (0.236 g, 0.439 mmol) was dissolved in dichloromethane (4.39 ml) under nitrogen to give a colorless solution. Bromotrimethylsilane (0.569 ml, 4.39 mmol) (Aldrich) was added and the reaction stirred for about 4 h. Solvents were removed under reduced pressure. Methanol (4 mL) and water (0.2 mL) were added and the solution was stirred for about 16 h. Solvents were removed under reduced pressure to give a brown oil/solid. Water was added and the solution sonicated while scraping the sides of the vial. The solution was stirred with a stir bar for about 1 h. The resulting solid was collected by vacuum filtration and washed with water and then pentane to provide 2-((1R,3S)-1-amino-3-(4-octylphenyl)cyclopentyl)ethylphosphonic acid (0.150 g, 0.393 mmol, 90% yield) as a off-white solid on drying under vacuum at 60° C.: LC/MS (method a) Rt=3.15 min.; MS m/z: 382.27 (M+H)+.

Workup

  1. customto give a colorless solution
  2. customSolvents were removed under reduced pressure
  3. additionMethanol (4 mL) and water (0.2 mL) were added
  4. stirringthe solution was stirred for about 16 h
  5. customSolvents were removed under reduced pressure
  6. customto give a brown oil/solid
  7. customthe solution sonicated
  8. stirringThe solution was stirred with a stir bar for about 1 h
  9. filtrationThe resulting solid was collected by vacuum filtration
  10. washwashed with water

Sources & evidence

ORD record
ord-3585de3b710441f784d0c4669f583a64
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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