Triphenylphosphine → HCID 18767693, compound

HRID 2105677Notes

Reaction equation

HRID 2105677 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][C:6](=O)[CH2:7][CH2:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]3[NH:25][C:24]4[C:23](=[O:26])[N:22]([CH2:27][CH2:28][CH3:29])[C:21](=[O:30])[N:20]([CH2:31][CH2:32][CH3:33])[C:19]=4[N:18]=3)([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)#[N:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Si]([N:58]=[N+:59]=[N-:60])(C)(C)C.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:30]=[C:21]1[N:20]([CH2:31][CH2:32][CH3:33])[C:19]2[N:18]=[C:17]([C:12]34[CH2:15][CH2:16][C:9]([CH2:8][CH2:7][C:6]5[N:5]([CH2:4][CH2:3][C:1]#[N:2])[N:60]=[N:59][N:58]=5)([CH2:14][CH2:13]3)[CH2:10][CH2:11]4)[NH:25][C:24]=2[C:23](=[O:26])[N:22]1[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 5462977Diethyl azodicarboxylateHCID 18767616HCID 18767616, compound

Product 1

HCID 18767693HCID 18767693, compoundYield 3.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(2-cyano-ethyl)-3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionamide (500 ng, 1.06 mmol, 1.0 eq), Ph3P (2.0 eq, 2.13 mmol, 560 mg), TMSN3 (2.0 eq, 2.13 mmol, 245 mg), and DEAD (2.0 eq, 2.13 mmol, 371 mg) in THF (10 ml) was stirred at rt for 24 h. The reaction vessel was re-charged with the reagent cocktail (2.0 eq, 2.13 mmol) and stirring was continued for an additional 24 h. The reaction was quenched by the addition of a 50% aqueous solution of (NH4)2Ce(NO3)6 and extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated in vacuo to afford a viscous orange oil. A portion of the material was purified by preparative LC to afford 20 mg of pure material. MS: 494 (MH+).

Workup

  1. additionThe reaction vessel was re-charged with the reagent cocktail (2.0 eq, 2.13 mmol)
  2. customThe reaction was quenched by the addition of a 50% aqueous solution of (NH4)2Ce(NO3)6
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto afford a viscous orange oil
  9. customA portion of the material was purified by preparative LC

Sources & evidence

ORD record
ord-475d56c461c64571b6f0c58f8e6972b8
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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