Triphenylphosphine → HCID 21357710, compound

HRID 507437Notes

Reaction equation

HRID 507437 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][CH:6]=C.[O:23]=[O+][O-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[C:4]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][CH:6]=[O:23]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 213577002-tert-Butoxycarbonylamino-2-phenyl-pent-4-enoic acid methyl ester

Product 1

HCID 21357710HCID 21357710, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of compound 12 (30.5 g, 0.1 mol) in CH2Cl2 (300 mL) at −78° C. was bubbled with O3 until the solution turned gray-blue. Then PPh3 (40 g, 0.15 mol) was added slowly to quench the reaction. After concentration, the residue was purified by column chromatography on silica gel (PE: EA=10:1) to give compound 13 (11 g, 35.8%). 1H NMR (400 MHz, CDCl3) δ 1.37 (s, 9 H), 3.57-3.61 (d, 1 H, J=18 Hz), 3.71 (s, 3H), 3.98-4.12 (m, 1 H), 6.16 (bs, 1 H), 7.31-7.43 (m, 5 H), 9.74 (s, 1H).

Workup

  1. customto quench
  2. customthe reaction
  3. concentrationAfter concentration
  4. customthe residue was purified by column chromatography on silica gel (PE: EA=10:1)

Sources & evidence

ORD record
ord-969e71edcf574dc99f13f71fd298f029
Source dataset
uspto-grants-2010_08
Patent number
US07786163B2

Reaction notes

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