Triphenylphosphine → HCID 12018743, compound

HRID 1860685Notes

Reaction equation

HRID 1860685 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][NH:21][CH:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]2O)=[CH:13][CH:12]=1)([CH3:9])[CH:7]=[CH2:8])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6]([CH3:9])([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:13][CH:12]=1)[CH:7]=[CH2:8])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 69899584HCID 69899584, compound

Product 1

HCID 12018743HCID 12018743, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of STEP 6 (0.32 g), ion powder (0.07 g), triphenylphosphine (0.21 g), and acetic acid (8 ml) was heated to reflux for 15 minutes. The solution was cooled, filtrated through a celite bed, and washed with ethyl acetate. The filtrate was concentrated. The crude product was purified on a silica gel column, eluting with dichloromethane/methanol/ammonium hydroxide (97.5:2:0.5) to afford colorless oil (0.26 g). The 1H NMR was consistent with the proposed structure.

Workup

  1. temperatureto reflux for 15 minutes
  2. temperatureThe solution was cooled
  3. filtrationfiltrated through a celite bed
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. customThe crude product was purified on a silica gel column
  7. washeluting with dichloromethane/methanol/ammonium hydroxide (97.5:2:0.5)

Sources & evidence

ORD record
ord-412d245fb8a3480a8640a8f13bcf7e42
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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