Water → HCID 67229016, compound

HRID 1785570Notes

Reaction equation

HRID 1785570 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27][C:28](=[O:43])[NH:29][C:30]1[C:39]2[CH2:38][CH:37]([N:40]=[N+]=[N-])[CH2:36][CH2:35][C:34]=2[CH:33]=[CH:32][CH:31]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C1COCC1>[CH2:20]([O:27][C:28](=[O:43])[NH:29][C:30]1[C:39]2[CH2:38][CH:37]([NH2:40])[CH2:36][CH2:35][C:34]=2[CH:33]=[CH:32][CH:31]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86609613HCID 86609613, compound

Product 1

HCID 67229016HCID 67229016, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Polymer supported triphenylphosphine (9.5 g, 28 mmol) was added to the product of Example 20B (4.6 g, 14 mmol) in THF (100 mL) containing 1.3 g (71 mmol) H2O. The mixture was stirred for 48 hours at ambient temperature, then diluted with THF and filtered through a pad of celite. The filter cake was washed with 3 solvents systems sequentially comprising 100% CH3OH, 1:1 CH3OH:CH2Cl2, and 100% CH2Cl2. The filtrate was concentrated under reduced pressure to provide 3.5 g (83%) of the title compound. 1H NMR (DMSO-d6) δ 8.81 (s, 1H), 7.45-7.30 (m, 5H), 7.13 (d, J=8 Hz, 1H), 7.05 (t, J=7 Hz, 1H), 6.90 (d, J=7 Hz, 1H), 5.12 (s, 2H), 3.00-2.65 (m, 4H), 2.23 (m, 1H), 1.84 (m, 1H), 1.59 (br s, 2H), 1.37 (m, 1H); MS (ESI+) m/z 297 (M+H)+.

Workup

  1. filtrationfiltered through a pad of celite
  2. washThe filter cake was washed with 3 solvents systems
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-06edc073ef404cf997477c31844ab0dc
Source dataset
uspto-grants-2009_03
Patent number
US07504520B2

Reaction notes

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