Bromotrimethylsilane → HCID 9856262, compound

HRID 2255473Notes

Reaction equation

HRID 2255473 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][N:11]1[CH2:18][CH2:17][NH:16][C:15]2[C:14](=[O:19])[C:13](=[O:20])[C:12]1=2)(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>ClCCCl>[O:19]=[C:14]1[C:13](=[O:20])[C:12]2[N:11]([CH2:10][CH2:9][P:4](=[O:3])([OH:5])[OH:8])[CH2:18][CH2:17][NH:16][C:15]1=2

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 10614286HCID 10614286, compound

Product 1

HCID 9856262HCID 9856262, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of [2-(7,8-dioxo-2,5-diazabicyclo[4.2.0]oct-1(6)-en-2-yl)ethyl]phosphonic acid diethyl ester (0.78 g, 2.6 mmol) and bromotrimethylsilane (2.1 mL, 16 mmol) in dry 1,2-dichloroethane (30 mL) was refluxed under nitrogen for 20 minutes. The cooled reaction mixture was concentrated in vacuo, and the residue was dissolved in water (100 mL) and washed with diethyl ether (3×50 mL). After concentrating the aqueous layer, the residue was recrystallized from water (25 mL) and methanol (300 mL) to yield a solid beige impurity which was removed by filtration. The filtrate was concentrated and recrystallized from water in isopropanol to yield the title compound as a yellow solid (0.37 g, 58%, mp 220°-270° C. dec); IR (KBr, cm-1): 1800; MS (-FAB): 245 (M-H); 1H NMR (DMSO/drop of DCl, 400 MHz): δ 3.58-3.51 (m, 2H), 3.40-3.33 (m, 4H), 2.07-1.98 (m, 2H).

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo
  3. dissolutionthe residue was dissolved in water (100 mL)
  4. washwashed with diethyl ether (3×50 mL)
  5. concentrationAfter concentrating the aqueous layer
  6. customthe residue was recrystallized from water (25 mL) and methanol (300 mL)
  7. customto yield a solid beige impurity which
  8. customwas removed by filtration
  9. concentrationThe filtrate was concentrated
  10. customrecrystallized from water in isopropanol

Sources & evidence

ORD record
ord-aa87d3a96cee4e51a3adda2f584129a6
Source dataset
uspto-grants-1993_08
Patent number
US05240946

Reaction notes

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