Bromotrimethylsilane → HCID 86591388, compound

HRID 1794465Notes

Reaction equation

HRID 1794465 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:31])[CH2:18][CH2:19][C:20]2[CH:21]=[N:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:12][CH:11]=1)([O:6]CC)=[O:5])[CH3:2].C[Si](Br)(C)C>C(#N)C>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:31])[CH2:18][CH2:19][C:20]2[CH:21]=[N:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:12][CH:11]=1)([OH:6])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 10138252HCID 10138252, compound

Product 1

HCID 86591388HCID 86591388, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-[4-(diethylphosphonomethyl)phenyl]-3-(5-phenyl-4-isoxazolyl)propionamide (221 mg), trimethylsilyl bromide (0.17 ml) and acetonitrile (10 ml) was stirred at room temperature for 16 hr. The reaction mixture was purified by preparative HPLC to give N-[4-(ethylphosphonomethyl)phenyl]-3-(5-phenyl-4-isoxazolyl)propionamide (139 mg, 67%). melting point: 80–82° C.

Workup

  1. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-a5dbaa7bca6a43a28a60e06f732e0ed7
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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