Triphenylphosphine → HCID 19909530, compound

HRID 1534369Notes

Reaction equation

HRID 1534369 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:20]=[N+:21]=[N-:22].[CH3:23][C:24]1[CH:29]=[C:28]([OH:30])[C:27]2[O:31][C:32]3[C:37]([C:38]([O:40][CH2:41][C:26]=2[CH:25]=1)=[O:39])=[C:36]([O:42][CH3:43])[C:35]([C@@H:44](O)[CH2:45][CH:46]([CH3:48])[CH3:47])=[CH:34][CH:33]=3.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.O1CCCC1.C(Cl)Cl>[N:20]([CH:44]([C:35]1[CH:34]=[CH:33][C:32]2[O:31][C:27]3[C:28]([OH:30])=[CH:29][C:24]([CH3:23])=[CH:25][C:26]=3[CH2:41][O:40][C:38](=[O:39])[C:37]=2[C:36]=1[O:42][CH3:43])[CH2:45][CH:46]([CH3:48])[CH3:47])=[N+:21]=[N-:22]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 24530Hydrazoic acidHCID 12421311-Hydroxy-3-(1-hydroxy-3-methylbutyl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-oneHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 19909530HCID 19909530, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

4.6 g (17.6 mmol) of triphenylphosphine and 29.3 ml of a freshly prepared 0.6 N solution of hydrazoic acid in toluene are added to 6 g (16.1 mmol) of penicillide (1b) in 100 ml of tetrahydrofuran. 2.7 ml (17.6 mmol) of diethyl azodicarboxylate are added dropwise to this mixture at 0° C. under argon. The mixture is then stirred at 25° C. for 12 h. After diluting with methylene chloride, the mixture is washed with aqueous bicarbonate, dried and evaporated. Chromatography on silica gel Si60 in diethyl ether/petroleum ether =2:1 yields 5.6 g (88% of theory) of colorless solid.

Workup

  1. washthe mixture is washed with aqueous bicarbonate
  2. customdried
  3. customevaporated
  4. customChromatography on silica gel Si60 in diethyl ether/petroleum ether =2:1 yields 5.6 g (88% of theory) of colorless solid

Sources & evidence

ORD record
ord-c234662dffc244a2b6992e641466fe03
Source dataset
uspto-grants-1992_02
Patent number
US05089487

Reaction notes

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