Acetonitrile → HCID 20205921, compound

HRID 543240Notes

Reaction equation

HRID 543240 reaction equation
C(O[C:5](=O)[C@:6]([NH:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH2:8][CH2:9][CH:10]([NH:12][C:13](=[O:20])C1C=CC=CC=1)N)N)C#C.[C:31](#N)[CH3:32].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO.C(Cl)(Cl)(Cl)Cl>[CH:5]([C:6]1([NH:21][C:22](=[O:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:8][CH2:9][CH2:10][NH:12][C:13]1=[O:20])=[C:31]=[CH2:32]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 54155829HCID 54155829, compound

Product 1

HCID 20205921HCID 20205921, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

An 11.04 g aliquot of 2,5-di(benzoylamino)ornithine propargyl ester was added to 80 ml of dry acetonitrile, 21.97 ml of triethylamine, 12.48 carbon tetrachloride and 30.69 g of triphenylphosphine. After about 2 hours at room temperature, 50 ml of methanol were added and the solution left at room temperature overnight. The reaction mixture was concentrated in vacuo, and to this residue was added 80 ml of tetrahydrofuran and 40 ml of 10% acetic acid and stirring. After 24 hours at room temperature, the reaction mixture was partitioned between ethyl acetate and 10% HCl. The organic layer was extracted several times with 10% HCl after which the combined aqueous fractions were washed exhaustively with methylene chloride. The pH of the aqueous portion was adjusted to 10 with concentrated sodium hydroxide to induce lactam formation. On cooling, a precipitate formed which was filtered and recrystallized from methanol-ethyl acetate to give the title compound, mp 203°-204° C.

Workup

  1. waitthe solution left at room temperature overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionto this residue was added 80 ml of tetrahydrofuran and 40 ml of 10% acetic acid
  4. waitAfter 24 hours at room temperature
  5. customthe reaction mixture was partitioned between ethyl acetate and 10% HCl
  6. extractionThe organic layer was extracted several times with 10% HCl after which the combined aqueous fractions
  7. washwere washed exhaustively with methylene chloride
  8. temperatureOn cooling
  9. customa precipitate formed which
  10. filtrationwas filtered
  11. customrecrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-b184215a63104623a2bb7650ac910ddc
Source dataset
uspto-grants-1987_04
Patent number
US04661510

Reaction notes

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