Bromotrimethylsilane → HCID 57554723, compound

HRID 1511905Notes

Reaction equation

HRID 1511905 reaction equation
C([O:3][P:4](/[CH:9]=[CH: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>ClCCl>[NH2:30][C@:11]1(/[CH:10]=[CH: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

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 57554734HCID 57554734, compound

Product 1

HCID 57554723HCID 57554723, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (1R,3S)-1-((E)-2-(diethoxyphosphoryl)vinyl)-3-(4-octylphenyl)cyclopentylcarbamate (0.2 g, 0.373 mmol) (10035787-0263) was dissolved in dichloromethane (3.73 ml) in a sealed vial to give a colorless solution. Bromotrimethylsilane (0.484 ml, 3.73 mmol) (Fluka) was added and the reaction stirred for about 16 h. Solvents were removed under reduced pressure to a thick oil. Methanol (4 mL) and water (0.2 mL) were added. The solution was sonicated and stirred, resulting in a cloudy reaction where a heavy precipitate forms. The solution was stirred for about 4 h. Add water (5 mL) and more product precipitated. The resulting solid was collected by vacuum filtration, washed with water and then pentane and dried under vacuum to provide (E)-2-((1R,3S)-1-amino-3-(4-octylphenyl)cyclopentyl)vinylphosphonic acid (0.117 g, 0.308 mmol, 83% yield) as a white solid: LCMS (method a) Rt=3.01 min.; MS m/z: 380.21 (M+H)+.

Workup

  1. customto give a colorless solution
  2. customSolvents were removed under reduced pressure to a thick oil
  3. additionMethanol (4 mL) and water (0.2 mL) were added
  4. customThe solution was sonicated
  5. stirringstirred
  6. customresulting in a cloudy reaction where a heavy precipitate forms
  7. stirringThe solution was stirred for about 4 h
  8. customAdd water (5 mL) and more product precipitated
  9. filtrationThe resulting solid was collected by vacuum filtration
  10. washwashed with water
  11. dry with materialpentane and dried under vacuum

Sources & evidence

ORD record
ord-46ec2084e0d844418ee8f8e6f1460b26
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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