Nitric Acid → HCID 67793562, compound

HRID 654863Notes

Reaction equation

HRID 654863 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C@@:12]2([CH2:18][N:19]3[CH:23]=[N:22][CH:21]=[N:20]3)[C@@H:15]([CH3:16])[C@@H:14]([CH3:17])[O:13]2)=[CH:8][CH:7]=1>C(OCC)C.CO>[N+:1]([O-:4])([OH:3])=[O:2].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C@@:12]2([CH2:18][N:19]3[CH:23]=[N:22][CH:21]=[N:20]3)[C@@H:15]([CH3:16])[C@@H:14]([CH3:17])[O:13]2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 57005851HCID 57005851, compound

Product 1

HCID 67793562HCID 67793562, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

0.19 ml of concentrated aqueous nitric acid (about 61%) was added to a solution of 300 mg (1.08 mmole) of (2R*,3S*,4R*)-2-(4-chlorophenyl)-3,4-dimethyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxetane (prepared as described in Example 20) in a mixture of 5 ml of diethyl ether and 1 ml of methanol. The resulting mixture was freed from the solvent by distillation under reduced pressure, and the resulting residue was mixed with a mixture of diethyl ether and hexane. The crystals which precipitated were collected by filtration, to give 351 mg (yield 95.4%) of the title compound, melting at 129°-142° C.

Workup

  1. distillationThe resulting mixture was freed from the solvent by distillation under reduced pressure
  2. additionthe resulting residue was mixed with a mixture of diethyl ether and hexane
  3. customThe crystals which precipitated
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-ab370420cfb849278f5fdada49001e1a
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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