Triphenylphosphine → HCID 89610343, compound

HRID 1507713Notes

Reaction equation

HRID 1507713 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:25]([OH:32])[C:24]([OH:33])=[C:23]2[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:18][CH:17]=1.[CH2:39]([O:46][CH2:47][CH2:48]O)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:39]([O:46][CH2:47][CH2:48][O:33][C:24]1[C:25]([OH:32])=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:22]([C:19]2[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=2)[C:23]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 121412-(Benzyloxy) ethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 71598928HCID 71598928, compound

Product 1

HCID 89610343HCID 89610343, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropyl azodicarboxylate (317 μL, 1.63 mmol) was added to a solution of diethyl 1-(4-fluorophenyl)-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate (UL2-003) (500 mg, 1.48 mmol), 2-(benzyloxy)ethanol (232 μL, 1.63 mmol) and triphenylphosphine (428 mg, 1.63 mmol) in DCM (5 ml), at 0° C. The reaction mixture was allowed to warm to RT and stirred for 1 h. The reaction was washed with water (5 mL) and the phases separated using a phase separation cartridge, the organic was concentrated in vacuo to afford a yellow oil. The residue was purified by silica gel chromatography (80 g, 0-25% EtOAc in isohexane) to afford diethyl 3-(2-(benzyloxy)ethoxy)-1-(4-fluorophenyl)-4-hydroxy-1H-pyrrole-2,5-dicarboxylate (22) (122 mg, 17%) as a yellow oil: m/z 472 (M+H)+ (ES+); 470 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 8.70 (s, 1H), 7.38-7.26 (m, 5H), 7.24-7.12 (m, 4H), 4.54 (s, 2H), 4.27-4.16 (m, 2H), 4.09-3.89 (m, 4H), 3.78-3.71 (m, 2H), 1.01-0.94 (m, 6H).

Workup

  1. washThe reaction was washed with water (5 mL)
  2. customthe phases separated
  3. customa phase separation cartridge
  4. concentrationthe organic was concentrated in vacuo
  5. customto afford a yellow oil
  6. customThe residue was purified by silica gel chromatography (80 g, 0-25% EtOAc in isohexane)

Sources & evidence

ORD record
ord-31e2e716a64843aeaf6da971e86eec90
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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