Water → HCID 70980750, compound

HRID 2281051Notes

Reaction equation

HRID 2281051 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:23]=[CH:22][C:14]3[N:15]([CH2:18][CH:19]4[CH2:21][CH2:20]4)[N:16]=[N:17][C:13]=3[C:12]=2[C:24]([F:27])([F:26])[F:25])=[CH:7][CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].[Na+].O>O1CCCC1>[CH:19]1([CH2:18][N:15]2[C:14]3[CH:22]=[CH:23][C:11]([C:8]4[CH:7]=[CH:6][C:5]([CH2:4][NH2:1])=[CH:10][CH:9]=4)=[C:12]([C:24]([F:27])([F:26])[F:25])[C:13]=3[N:17]=[N:16]2)[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 70978147HCID 70978147, compound

Product 1

HCID 70980750HCID 70980750, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

5-[4-(Azidomethyl)phenyl]-1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazole (162 mg, 0.435 mmol) and triphenylphosphine (342 mg, 1.30 mmol, 3 equiv) were combined in tetrahydrofuran (10 mL) at ambient temperature. After stirring for 5 minutes, the mixture was placed into a preheated oil bath at 50° C. for 2 hours. The mixture was treated with sodium bicarbonate (1.5 mL, aqueous saturated) and heated for an additional 1 hour at 50° C. The mixture was cooled to ambient temperature, poured into water (25 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (25 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 80:20; dichloromethane:methanol containing 10% ammonium hydroxide), providing the titled compound as a light green gum.

Workup

  1. waitthe mixture was placed into a preheated oil bath at 50° C. for 2 hours
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined organic extracts were washed with brine (25 mL)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel gradient chromatography (100:0 to 80:20; dichloromethane:methanol containing 10% ammonium hydroxide)

Sources & evidence

ORD record
ord-af26612caa2c470999676e7b465e02b8
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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