Bromotrimethylsilane → HCID 21972597, compound

HRID 2255472Notes

Reaction equation

HRID 2255472 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 (600 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-716de089945541a88d66067d9d0125d5
Source dataset
uspto-grants-1993_08
Patent number
US05240946

Reaction notes

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