Triphenylphosphine → HCID 86715088, compound

HRID 533894Notes

Reaction equation

HRID 533894 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:34][C@H:35]1[CH2:39][CH2:38][NH:37][C:36]1=[O:40].[F:41][C:42]1[CH:55]=[CH:54][C:45]([O:46][C:47]2[N:52]=[CH:51][C:50](O)=[CH:49][CH:48]=2)=[CH:44][CH:43]=1>C(Cl)Cl.C1COCC1>[F:41][C:42]1[CH:43]=[CH:44][C:45]([O:46][C:47]2[N:52]=[CH:51][C:50]([O:34][C@@H:35]3[CH2:39][CH2:38][NH:37][C:36]3=[O:40])=[CH:49][CH:48]=2)=[CH:54][CH:55]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11029774(3S)-3-hydroxypyrrolidin-2-oneHCID 59089027HCID 59089027, compound

Product 1

HCID 86715088HCID 86715088, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of THF (200 mL) and DCM (100 mL) under argon was added triphenylphosphine (polymer, 1.8 mmol/g, 20 g). Diisopropylazodicarboxylate (8.87 g) was added. After 5 minutes (S)-3-hydroxy-pyrrolidin-2-one (3.1 g) and 6-(4-fluoro-phenoxy)-pyridin-3-ol (6.0 g) were added. After 30 minutes the mixture was filtered and the filtrate concentrated. The residue was purified by chromatography (SiO2; DCM/MeOH 15:1) to provide the title compound. MS ESI+: m/z=289 [M+H]+.

Workup

  1. filtrationAfter 30 minutes the mixture was filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by chromatography (SiO2; DCM/MeOH 15:1)

Sources & evidence

ORD record
ord-44a970d9f18146598afefcafcc02e40b
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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