Methanol → HCID 46866646, compound

HRID 879965Notes

Reaction equation

HRID 879965 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([P:25]([O:31]C(C)C)([O:27]C(C)C)=[O:26])=[O:24])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](Br)(C)C.CO>C(Cl)(Cl)Cl.CC#N>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([P:25]([OH:31])([OH:27])=[O:26])=[O:24])(=[O:15])=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 76113BromotrimethylsilaneHCID 86661745HCID 86661745, compound

Product 1

HCID 46866646HCID 46866646, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To 1-[4-phenoxybenzenesulfonamido]-4-[diisopropylphosphonoformamido] butane (0.14 g, 0.27 mmol) in 5 ml CHCl3 was added TMSBr (5 eq, 1.9 ml, 14 mmol) and reaction was stirred and heated at 50° C. for 3 h. The reaction mixture was followed by 31P NMR. To the mixture reaction was added 5 ml MeOH for 1 h and the solvent was evaporated to give yellow oil, which solidified in MeCN to give 0.11 g (96%) white solid, m.p.=143-145° C. m/z [M+H]+ calcd/found 429/429.4.

Workup

  1. customTo the mixture reaction
  2. customthe solvent was evaporated
  3. customto give yellow oil, which

Sources & evidence

ORD record
ord-60f3c416fee443959dcde5e09ad914ea
Source dataset
uspto-grants-2015_03
Patent number
US08993544B2

Reaction notes

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