Triphenylphosphine → 6-Methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,3-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one

HRID 1597241Notes

Reaction equation

HRID 1597241 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]1([CH2:25][CH2:26][OH:27])[CH:24]=[CH:23][N:22]=[N:21]1.O[C:29]1[CH:38]=[C:37]2[C:32]([C:33](=[O:47])[N:34]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[CH:35]=[N:36]2)=[CH:31][C:30]=1[O:48][CH3:49].N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH3:49][O:48][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:29]=1[O:27][CH2:26][CH2:25][N:20]1[CH:24]=[CH:23][N:22]=[N:21]1)[N:36]=[CH:35][N:34]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:43])([CH3:44])[CH3:45])[C:33]2=[O:47]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 99892372-(1H-1,2,3-triazol-1-yl)ethan-1-olHCID 10804576(7-Hydroxy-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

Product 1

HCID 105971686-Methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,3-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-oneYield 276.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (2.82 g, 10.7 mmol) was added to a solution of 2-(1,2,3-triazol-1-yl)ethanol (609 mg, 5.4 mmol), (J. Antib. 1993, 46, 177), and 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin4-one (1.1 g, 3.6 mmol), (prepared as described for the starting material in Example 5), in methylene chloride (70 ml), diethyl azodicarboxylate (600 μl, 10.7 mmol) was then added. After stirring for 2 hours at ambient temperature, the volatiles were removed by evaporation and the residue was purified by column chromatography eluting with methylene chloride/methanol (98/2) to give 6-methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,3-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin4-one (4 g, 97%).

Workup

  1. custom(prepared
  2. customthe volatiles were removed by evaporation
  3. customthe residue was purified by column chromatography
  4. washeluting with methylene chloride/methanol (98/2)

Sources & evidence

ORD record
ord-6415c16d428b4f4097cf842a067599d3
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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