Triphenylphosphine → HCID 12018740, compound

HRID 1860670Notes

Reaction equation

HRID 1860670 reaction equation
[CH3:1][C:2]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N+:22]=2[O-])=[CH:12][CH:11]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Fe].C(O)(=O)C>[CH3:1][C:2]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:14][CH:15]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 178471300HCID 178471300, compound

Product 1

HCID 12018740HCID 12018740, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of the product of STEP 8 (150 mg, 0.33 mmol), iron powder (28 mg, 0.5 mmol), triphenylphosphine (87 mg, 0.33 mmol), and acetic acid (4.0 ml) was heated at reflux for 15 min. The cooled reaction was filtered through a short column of Celite®, and washed with ethyl acetate. The filtrate was concentrated. The residue was purified by chromatography (on silica gel, CH2Cl2/CH3OH/NH4OH-97.5/2/0.5) to afford a colorless oil in148 mg. The NMR spectra were consistent for the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 min
  3. customThe cooled reaction
  4. filtrationwas filtered through a short column of Celite®
  5. washwashed with ethyl acetate
  6. concentrationThe filtrate was concentrated
  7. customThe residue was purified by chromatography (on silica gel, CH2Cl2/CH3OH/NH4OH-97.5/2/0.5)
  8. customto afford a colorless oil in148 mg

Sources & evidence

ORD record
ord-6d06ba982aa74e049fba77a26e7212f7
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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