Chlorotrimethylsilane → HCID 13359892, compound

HRID 746069Notes

Reaction equation

HRID 746069 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P:11]([O-:15])[O:12][CH2:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C[Si](Cl)(C)C.C([C@@:35]1([C:44]([OH:46])=[O:45])[CH2:39][CH2:38][CH2:37][N:36]1[C:40](=[O:43])[CH2:41]Br)C1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:13]([O:12][P:11]([CH2:41][C:40]([N:36]1[CH2:37][CH2:38][CH2:39][C@H:35]1[C:44]([OH:46])=[O:45])=[O:43])([CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 18603696HCID 18603696, compoundHCID 86740835HCID 86740835, compound

Product 1

HCID 13359892HCID 13359892, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-phenylbutyl phosphonous acid, ethyl ester (0.24 g, 0.0011 mole) in chloroform (10 ml) was added triethylamine (0.34 ml, 0.002 mole) and the solution was cooled in an ice bath to 0° C. Trimethyl silyl chloride (0.29 ml, 0.0023 mole) was added to the above solution dropwise, followed by benzyl bromoacetyl-L-proline (0.25 g, 0.0011 mole). The ice bath was removed and the mixture stirred at room temperature for 4 hours and poured into 10% aqueous HCl (30 ml) and crushed ice (20 g). After shaking the mixture in a separatory funnel, the chloroform layer was separated and the aqueous layer extracted with dichloromethane (2×50 ml). The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and the solvents removed on a rotavap. The resulting crude thick oil was vacuum dried to get 0.23 g (57%) of title compound, TLC: silica gel, CH2Cl2 :MeOH:HOAc shows one main spot at Rf =0.23.

Workup

  1. customThe ice bath was removed
  2. additionpoured into 10% aqueous HCl (30 ml)
  3. customcrushed ice (20 g)
  4. stirringAfter shaking the mixture in a separatory funnel
  5. customthe chloroform layer was separated
  6. extractionthe aqueous layer extracted with dichloromethane (2×50 ml)
  7. washThe combined organic phase was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvents removed on a rotavap
  10. customdried

Sources & evidence

ORD record
ord-58b9b0734bb343869acd7a155932dabf
Source dataset
uspto-grants-1986_07
Patent number
US04602092

Reaction notes

Loading…