Trimethylsilyl iodide → HCID 54399964, compound

HRID 442809Notes

Reaction equation

HRID 442809 reaction equation
[NH2:1][C:2]([C:21]1[CH:26]=[CH:25][C:24]([P:27]([O:32]CC)([O:29]CC)=[O:28])=[CH:23][CH:22]=1)([CH2:6][CH:7]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]([OH:5])=[O:4].C[Si](I)(C)C>ClCCl>[NH2:1][C:2]([C:21]1[CH:22]=[CH:23][C:24]([P:27]([OH:29])([OH:32])=[O:28])=[CH:25][CH:26]=1)([CH2:6][CH:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[O:14][C:15]2[C:20]1=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 53832874HCID 53832874, compound

Product 1

HCID 54399964HCID 54399964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-amino-3-(9H-xanthen-9-yl)-2-(4-diethylphosphonophenyl)propanoic acid (114 mg, 0.25 mmol) in dry dichloromethane (10 ml) stirred under an atmosphere of nitrogen was added trimethylsilyl iodide (0.26 g, 1.29 mmol). The resulting solution was stirred at room temperature for 24 h and then further trimethylsilyl iodide (0.26 g, 1.29 ml) added. Stirring was continued for 5 h, the reaction mixture evaporated to dryness and redissolved in water. Ion exchange chromatography using the conditions described in Example 1 (vi) gave the title compound as a pale yellow powder.

Workup

  1. stirringThe resulting solution was stirred at room temperature for 24 h
  2. stirringStirring
  3. customthe reaction mixture evaporated to dryness
  4. dissolutionredissolved in water

Sources & evidence

ORD record
ord-e32744ea747f4fffb8aa59a799af21da
Source dataset
uspto-grants-1999_04
Patent number
US05891899

Reaction notes

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