Triphenylphosphine → HCID 22107091, compound

HRID 1456623Notes

Reaction equation

HRID 1456623 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][N:40]=[N:39]1.N(C(OCC)=O)=N[C:45](OCC)=O>O1CCCC1.C(Cl)(Cl)Cl>[N:38]1[N:39]([CH:5]2[CH2:6][CH:7]([C:9]([O:11][CH3:45])=[O:10])[NH:8][C:12]2=[O:14])[N:40]=[N:41][CH:42]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54262066HCID 54262066, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 22107091HCID 22107091, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the compound prepared as described in Example 4 (318 mg), triphenylphosphine (577 mg), and tetrazole (155 mg) in dry tetrahydrofuran (4.5 ml) was cooled in an ice/water bath, 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 171/2 hours, the reaction solution was concentrated in vacuo to give a greasy crystalline mass. This material was diluted with chloroform (10 ml) and concentrated in vacuo. This procedure was repeated to remove traces of tetrahydrofuran. The residue was dissolved in chloroform (10 ml) and purified by centrifugal thin-layer chromatography, eluting with ethyl acetate/hexane (1:1) followed by ethyl acetate/hexane (9:1), ethyl acetate, ethyl acetate/methanol (9:1), and ethyl acetate/methanol (4:1). The first isomer to elute was the tetrazol-2-yl compound, and the second isomer to elute was the tetrazol-1-yl compound. Fractions containing each of these isomers in pure form were pooled and concentrated in vacuo. The residue was triturated in methylene chloride (3 ml), and the title compounds isolated by filtration to give 46 mg of the tetrazol-2-yl compound and 227 mg of the tetrazol-1-yl compound.

Workup

  1. additionA mixture of the compound
  2. customprepared
  3. temperaturewas cooled in an ice/water bath
  4. additionAfter the addition
  5. concentrationAfter about 171/2 hours, the reaction solution was concentrated in vacuo
  6. customto give a greasy crystalline mass
  7. concentrationconcentrated in vacuo
  8. customto remove traces of tetrahydrofuran
  9. dissolutionThe residue was dissolved in chloroform (10 ml)
  10. custompurified by centrifugal thin-layer chromatography
  11. washeluting with ethyl acetate/hexane (1:1)
  12. washThe first isomer to elute
  13. washthe second isomer to elute
  14. additionFractions containing each of these isomers in pure form
  15. concentrationconcentrated in vacuo
  16. customThe residue was triturated in methylene chloride (3 ml)

Sources & evidence

ORD record
ord-3093ace932f543e4aa4a8abbc703fcd2
Source dataset
uspto-grants-1998_12
Patent number
US05843997

Reaction notes

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