Hydrochloric Acid → HCID 19973110, compound

HRID 2380325Notes

Reaction equation

HRID 2380325 reaction equation
O[CH2:2][CH2:3][NH:4][C:5](=[O:25])[C:6]([F:24])([F:23])[C:7]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22])([OH:14])[CH2:8][N:9]1[CH:13]=[N:12][CH:11]=[N:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.Cl>O.C(OCC)(=O)C.O1CCCC1>[N:4]1([C:5]([C:6]([F:24])([F:23])[C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])([OH:14])[CH2:8][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[O:25])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19973077HCID 19973077, compound

Product 1

HCID 19973110HCID 19973110, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 10 ml of dried tetrahydrofuran were added 0.36 g of N-(2-hydroxyethyl)-3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanamide, 0.39 g of triphenylphosphine and 0.26 g of diethyl azodicarboxylate. The resulting mixture was subjected to reaction at 20°-25° C. for 12 hours. The reaction mixture was introduced into a mixed solvent consisting of 20 ml of ethyl acetate and 10 ml of water. The resulting solution was adjusted to pH 2.0 with 6N hydrochloric acid. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluant: toluene/ethyl acetate=10/1) to obtain 0.13 g of 1-aziridinylcarbonyl-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propane.

Workup

  1. customThe resulting mixture was subjected to reaction at 20°-25° C. for 12 hours
  2. additionThe reaction mixture was introduced into a mixed solvent
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThereafter, the solvent was removed by distillation under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by a column chromatography (eluant: toluene/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-cdfe70f70c7944abbc7283bb4528bdf1
Source dataset
uspto-grants-1994_11
Patent number
US05366989

Reaction notes

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