1H-1,2,4-Triazole → HCID 54136983, compound

HRID 1900620Notes

Reaction equation

HRID 1900620 reaction equation
CC1C=CC=CC=1O[CH:5]([C:12]([OH:14])=O)[CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:38]1[CH:42]=[N:41][CH:40]=[N:39]1.N(C(OCC)=O)=N[C:45](OCC)=O>O1CCCC1.C(Cl)(Cl)Cl>[N:38]1([CH:5]2[CH2:6][CH:7]([C:9]([O:11][CH3:45])=[O:10])[NH:8][C:12]2=[O:14])[CH:42]=[N:41][CH:40]=[N:39]1

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54262066HCID 54262066, compound

Product 1

HCID 54136983HCID 54136983, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of the compound prepared as described in Example 4 (318 mg), triphenylphosphine (577 mg), and 1,2,4-triazole (152 mg) in dry tetrahydrofuran (4.5 ml) was cooled to about 5° C., and treated with diethyl azodicarboxylate (383 mg) over a ten minute period. After the addition was complete, the reaction was allowed to warm to room temperature. After about 17 hours, the reaction solution was concentrated in vacuo and allowed to stand at room temperature under reduced pressure to give a crystalline solid. This solid was diluted with chloroform and purified by centrifugal thin-layer chromatography, eluting with ethyl acetate/hexane (1:1) followed by ethyl acetate/hexane (3:1), ethyl acetate, ethyl acetate/methanol (19:1), and ethyl acetate/methanol (9:1). The fractions containing the title compound were combined and concentrated in vacuo to give 280 mg.

Workup

  1. additionA mixture of the compound
  2. customprepared
  3. additionAfter the addition
  4. temperatureto warm to room temperature
  5. concentrationthe reaction solution was concentrated in vacuo
  6. customto stand at room temperature under reduced pressure
  7. customto give a crystalline solid
  8. custompurified by centrifugal thin-layer chromatography
  9. washeluting with ethyl acetate/hexane (1:1)
  10. additionThe fractions containing the title compound
  11. concentrationconcentrated in vacuo
  12. customto give 280 mg

Sources & evidence

ORD record
ord-908c82af68e64b51a717753ad0d2430e
Source dataset
uspto-grants-1996_11
Patent number
US05576323

Reaction notes

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