Triphenylphosphine → HCID 131719534, compound

HRID 741694Notes

Reaction equation

HRID 741694 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[C:15](/[CH:19]=[CH:20]\[CH2:21]O)[CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:42]([O:46][C:47]([NH:49][O:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[O:48])([CH3:45])([CH3:44])[CH3:43].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:42]([O:46][C:47]([N:49]([CH2:21]/[CH:20]=[CH:19]\[C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:10]2[CH2:9][CH:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[O:12][N:11]=2)[CH:14]=1)[O:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[O:48])([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2728863tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamateHCID 5462977Diethyl azodicarboxylateHCID 67732574HCID 67732574, compound

Product 1

HCID 131719534HCID 131719534, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the product of Step 3, above (15, 1.8 g, 6 mmol), PPh3 (1.9 g, 7.2 mmol) and N,O-di-tert-butoxycarbonylhydroxylamine (1.85 g, 7.8 mmol) in THF (25 ml) was added dropwise a solution of diethylazodicarboxylate (1.2 ml, 7.2 mmol) in THF (5 ml) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 1.5 hours and solvent was removed under reduced pressure. The resultant residue was purified by column chromatography on silica gel (eluent=ethyl acetate:n-hexane, 1:7) to afford 3.0 g (98% yield) of the title compound (16) as a colorless oil.

Workup

  1. customsolvent was removed under reduced pressure
  2. customThe resultant residue was purified by column chromatography on silica gel (eluent=ethyl acetate:n-hexane, 1:7)

Sources & evidence

ORD record
ord-ca793b63c88841f684156bd4cc518304
Source dataset
uspto-grants-1996_09
Patent number
US05552424

Reaction notes

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