Triethylamine → HCID 178501870, compound

HRID 490947Notes

Reaction equation

HRID 490947 reaction equation
C(N(CC)CC)C.C([SiH](CC)CC)C.[CH3:15][O:16][C:17](=[O:62])[CH:18]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([NH:44][C:45]([NH:54][C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])=[N:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH:39]=1)[O:19][P:20]([C@@H:23]([NH:27]C(OCC1C=CC=CC=1)=O)[CH:24]([CH3:26])[CH3:25])([OH:22])=[O:21]>C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15][O:16][C:17](=[O:62])[CH:18]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([NH:44][C:45]([NH:54][C:55]([O:57][C:58]([CH3:59])([CH3:61])[CH3:60])=[O:56])=[N:46][C:47]([O:49][C:50]([CH3:52])([CH3:53])[CH3:51])=[O:48])[CH:39]=1)[O:19][P:20]([C@@H:23]([NH2:27])[CH:24]([CH3:26])[CH3:25])([OH:22])=[O:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 178501871HCID 178501871, compound

Product 1

HCID 178501870HCID 178501870, compoundYield 116%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of palladium(II) acetate (184 mg, 0.82 mmol) in 13 mL of CH2Cl2 was added triethylamine (0.24 mL, 1.72 mmol) and triethylsilane (1.80 mL, 11.3 mmol). After stirring the resulting black slurry for 25 minutes, 2-(3-(N′,N″-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1R)-(1-(benzyloxycarbonyl)amino-2-methylpropyl)(hydroxy)phosphinoyloxy)ethanoic acid methyl ester (2.93 g, 4.23 mmol) in methylene chloride (3 mL) was added. The reaction mixture was stirred at ambient temperature for 5.5 hours at which point the reaction was concentrated in vacuo, dissolved in methanol, and filtered. The filtrate was concentrated in vacuo and placed in vacuo overnight to provide 2.7143 g (116%) of 2-(3-(N′,N″-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1R)-(1-amino-2-methylpropyl)-(hydroxy)phosphinoyloxy)ethanoic acid methyl ester as an impure white foam.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 5.5 hours at which
  2. concentrationwas concentrated in vacuo
  3. dissolutiondissolved in methanol
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customplaced in vacuo overnight

Sources & evidence

ORD record
ord-0ddda1853d294cdf867bc8961f33d948
Source dataset
uspto-grants-2009_05
Patent number
US07528173B2

Reaction notes

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