Bromotrimethylsilane → HCID 178527082, compound

HRID 582193Notes

Reaction equation

HRID 582193 reaction equation
C[Si](Br)(C)C.[F:6][CH:7]([P:17]([OH:20])(=[O:19])[OH:18])[CH2:8][CH:9]([O:15]C)[C:10]1[N:14]=[CH:13][NH:12][N:11]=1>ClCCl.CCOCC>[F:6][CH:7]([P:17]([OH:20])(=[O:18])[OH:19])[CH2:8][CH:9]([OH:15])[C:10]1[N:14]=[CH:13][NH:12][N:11]=1

Participants

5

Reactant 2

HCID 76113BromotrimethylsilaneHCID 178495101HCID 178495101, compound

Product 1

HCID 178527082HCID 178527082, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of this material in dichloromethane was treated with trimethylsilyl bromide as described in Example 24 to give, after ion-exchange chromatography, 1-fluoro-3-methoxy-3(1,2,4-triazol-3-yl) propane phosphonic acid (Compound No. 46 in Table 1) also as a mixture of diastereoisomers in a ratio of 3:1 or 1:3. NMR(D2O): δ 2.15-2.4(2H,m); 3.25(3H,s); 4.4-4.8(1H,m); 4.85(1H,t); 8.9(1H,2 xs). FAB M/S: MH+ 240. More vigorous deprotection, for example in the presence of iodide ion, will result in ether cleavage to give 1-fluoro-3-hydroxy-3(1,2,4-triazol-3-yl)propane phosphonic acid (Compound No. 45 in Table 1), also as a mixture of diastereoisomers.

Workup

  1. customto give

Sources & evidence

ORD record
ord-75fefc3201004c0d94df8fe659bf85cd
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

Loading…