Triphenylphosphine → HCID 59463758, compound

HRID 908512Notes

Reaction equation

HRID 908512 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([N:28]1[C:33](=[O:34])[CH:32]=[CH:31][NH:30][C:29]1=[O:35])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:36]([O:55][CH2:56]/[CH:57]=[CH:58]/[CH2:59]O)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CCCCCC.CCOC(C)=O>[C:20]([N:28]1[C:33](=[O:34])[CH:32]=[CH:31][N:30]([CH2:59]/[CH:58]=[CH:57]/[CH2:56][O:55][C:36]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:29]1=[O:35])(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5695133-BenzoyluracilHCID 5363146Diisopropyl azodicarboxylateHCID 10882092(E)-4-(Trityloxy)but-2-en-1-ol

Product 1

HCID 59463758HCID 59463758, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Polymer bound triphenylphosphine (0.75 g, 2.25 mmol) was shaken in THF (5 ml) for 15 minutes, then 3-benzoyluracil (290 mg, 1.35 mmol), trityl alcohol (11) (300 mg, 0.90 mmol) were added to the suspension of the resin. A solution of DIAD (0.354 ml, 1.80 mmol) in THF (2 ml) was added to the mixture. The reaction was shaken 24 hours at room temperature and monitored by TLC (Hexane/EtOAc 50:50). The resin was filtered and washed twice with THF (5 ml). The filtrate was concentrated under reduced pressure and taken in EtOAc (5 ml), a white solid precipitated. The precipitate was filtered; the filtrate was concentrated again and purified by flash chromatography using Hexane/EtOAc 40:60→60:40 as gradient which gave the title compound as a white foam (222 mg, 48%). Rf: 0.55 in Hexane/EtOAc 50:50 (UV/PMA).

Workup

  1. filtrationThe resin was filtered
  2. washwashed twice with THF (5 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customa white solid precipitated
  5. filtrationThe precipitate was filtered
  6. concentrationthe filtrate was concentrated again
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-fe0d7a7efd334c18a899370df3e07154
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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