Bromotrimethylsilane → HCID 9860385, compound

HRID 2255477Notes

Reaction equation

HRID 2255477 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][N:11]1[CH2:19][CH:18]([OH:20])[CH2:17][NH:16][C:15]2[C:14](=[O:21])[C:13](=[O:22])[C:12]1=2)(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>ClCCCl.O>[OH:20][CH:18]1[CH2:17][NH:16][C:15]2[C:14](=[O:21])[C:13](=[O:22])[C:12]=2[N:11]([CH2:10][CH2:9][P:4](=[O:3])([OH:5])[OH:8])[CH2:19]1

Participants

5

Reactant 2

HCID 76113BromotrimethylsilaneHCID 10592653HCID 10592653, compound

Product 1

HCID 9860385HCID 9860385, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of [2-(4-hydroxy-8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethyl]phosphonic acid diethyl ester (2.5 g, 7.5 mmol) in dry 1,2-dichloroethane (100 mL) under nitrogen, was added bromotrimethylsilane (9.2 mL, 60 mmol). The reaction mixture was refluxed for 20 min and then concentrated in vacuo to yield a yellow-orange foam, which was dissolved in water (100 mL). The water was washed with ether (3×100 mL) and then concentrated in vacuo to yield a solid which was recrystallized from water in isopropanol to yield [2-(4-hydroxy-8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethyl]phosphonic acid one sixth hydrate as a pale yellow solid (1.79 g, 86%, mp 268°-270° C. dec); IR (KBr, cm-1): 3480, 3220, 1820; MS (-FAB): 275 (M-H, 22), 148 (100); 1H NMR (DMSO 1 drop of DCl, 400 MHz): δ 3.90 (m, 1H), 3.85-3.74 (m, 2H), 3.46 (d, J=13 Hz, 1H), 3.34 (d of d, J=13 and 7 Hz, 1H), 3.28 (m, 2H), 1.98-1.89 (m, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 20 min
  2. concentrationconcentrated in vacuo
  3. customto yield a yellow-orange foam, which
  4. washThe water was washed with ether (3×100 mL)
  5. concentrationconcentrated in vacuo
  6. customto yield a solid which
  7. customwas recrystallized from water in isopropanol

Sources & evidence

ORD record
ord-0daac17d7fa949ba8076ad3f0bcf7775
Source dataset
uspto-grants-1993_08
Patent number
US05240946

Reaction notes

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