Triphenylphosphine → HCID 90997563, compound

HRID 1364010Notes

Reaction equation

HRID 1364010 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:10]([N:11]=[N+:12]=[N-:13])[CH2:9][C:8](C(OCC)=O)=[CH:7][C@@H:6]1[OH:19])(=[O:3])[CH3:2].C1([P:26]([O-:29])(=[O:28])[O-:27])CCCCC=1.[CH:30]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:31]=1.[CH3:49][CH:50](OC(/N=N/C(OC(C)C)=O)=O)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>C1COCC1>[C:1]([NH:4][C@@H:5]1[C@@H:10]([N:11]=[N+:12]=[N-:13])[CH2:9][C:8]([P:26]([O:27][CH2:49][CH3:50])(=[O:28])[O:29][CH2:30][CH3:31])=[CH:7][C@@H:6]1[OH:19])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 5363146Diisopropyl azodicarboxylateHCID 23419955HCID 23419955, compoundHCID 46223766HCID 46223766, compound

Product 1

HCID 90997563HCID 90997563, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By a procedure similar to that for 9a, compound 8b (1.67 g, 4.8 mmol) was treated with Ph3P (2.42 g, 9.2 mmol), freshly distilled DIAD (1.86 g, 9.2 mmol) and DPPA (2.54 g, 9.2 mmol) in THF (45 mL) for 48 h at room temperature to give the corresponding azide product (1.39 g, 78% yield) after purification by flash column chromatography (60% EtOAc/hexane, 3:2). The subsequent hydrolysis in refluxing EtOH/HCl (1 M aqueous solution) gave the desired product 9b (1.18 g, 95% yield), which was used directly for the preparation of 10b.

Sources & evidence

ORD record
ord-c646b3a1929f415db65f2bf4ac1e9c80
Source dataset
uspto-grants-2011_02
Patent number
US07888337B2

Reaction notes

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