Bromotrimethylsilane → HCID 21972597, compound

HRID 1681063Notes

Reaction equation

HRID 1681063 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][NH:11][CH2:12][C:13]1[C:16](=[O:17])[C:15](=[O:18])[C:14]=1[NH2:19])(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>ClCCCl>[NH2:19][C:14]1[C:15](=[O:18])[C:16](=[O:17])[C:13]=1[CH2:12][NH:11][CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 57010612HCID 57010612, compound

Product 1

HCID 21972597HCID 21972597, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of [2-[(2-amino-3,4-dioxo-1-cyclobuten-1-yl)methylamino]ethyl]phosphonic acid diethyl ester (660 mg, 2.3 mmol) in anhydrous 1,2-dichloroethane (20 mL) under nitrogen was treated with bromotrimethylsilane (2.0 mL, 15 mmol) and heated to reflux for 10 minutes. The yellow solution was concentrated and the resulting solid was dissolved in water (75 mL), washed with diethyl ether (2×50 mL) and evaporated. The solid was dissolved in boiling methanol, filtered, and concentrated with the addition of ethyl acetate to a final volume of 75 mL to afford the title compound as a yellow solid (310 mg, 58%, mp 230°-260° C. dec); IR (KBr, cm-1): 3340, 1800; MS (-FAB): 233 (M-H, 32), 148 (100); 1H NMR (DMSO, 400 MHz): δ 7.62 (br s, NH2), 3.68 (br s, 2H), 3.16 (br s, 3 H), 1.90 (d of t, J=18 and 7.5 Hz, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 10 minutes
  3. concentrationThe yellow solution was concentrated
  4. dissolutionthe resulting solid was dissolved in water (75 mL)
  5. washwashed with diethyl ether (2×50 mL)
  6. customevaporated
  7. dissolutionThe solid was dissolved
  8. filtrationfiltered
  9. concentrationconcentrated with the addition of ethyl acetate to a final volume of 75 mL

Sources & evidence

ORD record
ord-386ade9f70ff4714b75a5af5f42ac456
Source dataset
uspto-grants-1992_12
Patent number
US05168103

Reaction notes

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